Terpene/Terpenoid Mega Thread [Archive]

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c-ray

09-26-2008, 04:09 PM

okay here we go folks, time to start discussing and researching the aromatic components of Cannabis...bring it on, everything we know and want to know..

firstly some info from Wikipedia:
Terpene (http://en.wikipedia.org/wiki/Terpene)
From Wikipedia, the free encyclopedia

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as swallowtail butterflies, which emit terpenes from their osmeterium.

They are the major components of resin, and of turpentine produced from resin. The name "terpene" is derived from the word "turpentine". In addition to their roles as end-products in many organisms, terpenes are major biosynthetic building blocks within nearly every living creature. Steroids, for example, are derivatives of the triterpene squalene.

When terpenes are modified chemically, such as by oxidation or rearrangement of the carbon skeleton, the resulting compounds are generally referred to as terpenoids. Some authors will use the term terpene to include all terpenoids. Terpenoids are also known as Isoprenoids.

Terpenes and terpenoids are the primary constituents of the essential oils of many types of plants and flowers. Essential oils are used widely as natural flavor additives for food, as fragrances in perfumery, and in traditional and alternative medicines such as aromatherapy. Synthetic variations and derivatives of natural terpenes and terpenoids also greatly expand the variety of aromas used in perfumery and flavors used in food additives. Vitamin A is an example of a terpene.

Structure and biosynthesis

Terpenes are derived biosynthetically from units of isoprene, which has the molecular formula C5H8. The basic molecular formulae of terpenes are multiples of that, (C5H8)n where n is the number of linked isoprene units. This is called the isoprene rule or the C5 rule. The isoprene units may be linked together "head to tail" to form linear chains or they may be arranged to form rings. One can consider the isoprene unit as one of nature's common building blocks.

Isoprene itself does not undergo the building process, but rather activated forms, isopentenyl pyrophosphate (IPP or also isopentenyl diphosphate) and dimethylallyl pyrophosphate (DMAPP or also dimethylallyl diphosphate), are the components in the biosynthetic pathway. IPP is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, totally unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP(2-Methyl-D-erythritol-4-phosphate)-pathway, which is initiated from C5-sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase.

As chains of isoprene units are built up, the resulting terpenes are classified sequentially by size as hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and tetraterpenes.

Types

Terpenes may be classified by the number of terpene units in the molecule; a prefix in the name indicates the number of terpene units needed to assemble the molecule. A single terpene unit is formed from two molecules of isoprene, so that a monoterpene consists of one terpene but two isoprene units.

Hemiterpenes consist of a single isoprene unit. Isoprene itself is considered the only hemiterpene, but oxygen-containing derivatives such as prenol and isovaleric acid are hemiterpenoids.
Monoterpenes consist of two isoprene units and have the molecular formula C10H16. Examples of monoterpenes are: geraniol, limonene and terpineol.
Sesquiterpenes consist of three isoprene units and have the molecular formula C15H24. Examples of sesquiterpenes are: farnesol. The sesqui- prefix means one and a half.
Diterpenes are composed for four isoprene units and have the molecular formula C20H32. They derive from geranylgeranyl pyrophosphate. Examples of diterpenes are cafestol, kahweol, cembrene and taxadiene (precursor of taxol). Diterpenes also form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory. The herb Sideritis contains diterpenes.
Sesterterpenes, terpenes having 25 carbons and five isoprene units, are rare relative to the other sizes. The sester- prefix means half to three, i.e. two and a half.
Triterpenes consist of six isoprene units and have the molecular formula C30H48. The linear triterpene squalene, the major constituent of shark liver oil, is derived from the reductive coupling of two molecules of farnesyl pyrophosphate. Squalene is then processed biosynthetically to generate either lanosterol or cycloartenol, the structural precursors to all the steroids.
Tetraterpenes contain eight isoprene units and have the molecular formula C40H64. Biologically important tetraterpenes include the acyclic lycopene, the monocyclic gamma-carotene, and the bicyclic alpha- and beta-carotenes.
Polyterpenes consist of long chains of many isoprene units. Natural rubber consists of polyisoprene in which the double bonds are cis. Some plants produce a polyisoprene with trans double bonds, known as gutta-percha.

and

Terpenoid (http://en.wikipedia.org/wiki/Terpenoid)
From Wikipedia, the free encyclopedia

The terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally-occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in functional groups but also in their basic carbon skeletons. These lipids can be found in all classes of living things, and are the largest group of natural products.

Plant terpenoids are used extensively for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial, antineoplastic, and other pharmaceutical functions. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, and the color of yellow flowers. Well-known terpenoids include citral, menthol, camphor, Salvinorin A in the plant Salvia divinorum, and the cannabinoids found in Cannabis.

The steroids and sterols in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to proteins, e.g., to enhance their attachment to the cell membrane; this is known as isoprenylation.

Many of these are substrates for plant Cytochrome P450.

Structure and classification

Terpenes are hydrocarbons resulting from the combination of several isoprene units. Terpenoids can be thought of as modified terpenes, wherein methyl groups have been moved or removed, or oxygen atoms added. (Some authors use the term "terpene" more broadly, to include the terpenoids.) Just like terpenes, the terpenoids can be classified according to the number of isoprene units used:

Monoterpenoids, 2 isoprene units
Sesquiterpenoids, 3 isoprene units
Diterpenoids, 4 isoprene units
Sesterterpenoids, 5 isoprene units
Triterpenoids, 6 isoprene units
Tetraterpenoids, 8 isoprene units
Polyterpenoids with a larger number of isoprene units

Terpenoids can also be classified according to the number of cyclic structures they contain.

and also

Essential oil (http://en.wikipedia.org/wiki/Essential_oil)
From Wikipedia, the free encyclopedia

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material from which they were extracted, such as oil of clove. An oil is "essential" in the sense that it carries a distinctive scent, or essence, of the plant. Essential oils do not as a group need to have any specific chemical properties in common, beyond conveying characteristic fragrances. They are not to be confused with essential fatty acids.

Essential oils are generally extracted by distillation. Other processes include expression, or solvent extraction. They are used in perfumes, cosmetics and bath products, for flavoring food and drink, and for scenting incense and household cleaning products.

Various essential oils have been used medicinally at different periods in history. Medical applications proposed by those who sell medicinal oils range from skin treatments to remedies for cancer, and are often based on historical use of these oils for these purposes. Such claims are now subject to regulation in most countries, and have grown correspondingly more vague, to stay within these regulations.

Interest in essential oils has revived in recent decades, with the popularity of aromatherapy, a branch of alternative medicine which claims that the specific aromas carried by essential oils have curative effects. Oils are volatilized or diluted in a carrier oil and used in massage, or burned as incense, for example.

c-ray

09-26-2008, 04:28 PM

List of Terpenes/Terpenoids Present in Cannabis

I will keep adding to this post all the aromatic compounds that I find referenced in various analyses of Cannabis...

trans-anethol
allo-aromadendrene
α-bergamotene
cis-α-bergamotene
trans-α-bergamotene
β-bisabolene
β-bourbonene
hexyl butyrate
Δ-cadinene
γ-cadinene
camphene
Δ3-carene
caryophyllene oxide
β-caryophyllene
isocaryophyllene
α-copaene
curcumene
para cymene-8-ol
β-farnesene
trans-β-farnesene
germacrene B
α-guaiene
hexyl hexanoate
α-humulene
epoxy humulene
α,β-unsaturated ketone
linalool
limonene
trans-linalool oxide
α-muurolene
γ-muurolene
myrcene
β-myrcene
nerolidol
cis-epoxy-ocimene
trans-β-ocimene
β-phellandrene
phtalic acid diethyl ester
α-pinene
β-pinene
sabicene hydrate
selina-3,7(11)-diene
α-selinene
7-epi-α-selinene
β-selinene
γ-selinene
β-sesquiphellandrene
spathulenol
terpinene-4-ol
α-terpinene
γ-terpinene
α-terpineol
terpinolene
epoxy-terpinolene
α-ylangene

c-ray

09-26-2008, 04:40 PM

from http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=43&issue=12&startPage=3372

ESSENTIAL OILS AND THEIR CONSTITUENTS
XX1X.l THE ESSENTIAL OIL OF MARIHUANA:
COMPOSITION OF GENUINE INDIAN CANNABIS SATIVA L.
K. L. HANDA, I. C. NIGAM AND LEO LEVI
Pharmaceutical Chenzistry Division, Food and Drug Directorate, Ottawa, Canada
Received July 2, 1965

ABSTRACT
The essential oil obtained by hydrodistillation of freshly harvested Indian Cannabis sativa was found to contain the following constituents that have not previously been reported:
α-pinene, camphene, β-pinene, α-terpinene, β-phellandrene, γ-terpinene, linalool, trans-linalool oxide, sabicene hydrate, α-bergamotene, terpinene-4-ol, β-farnesene, α-terpineol, α-selinene, curcumene, and caryophyllene oxide. The presence of trace amounts of two alcohols and of an α,β-unsaturated ketone, for which gas chromatographic and spectral characteristics are recorded, was also detected

c-ray

09-26-2008, 04:48 PM

from http://findarticles.com/p/articles/mi_qa4091/is_200305/ai_n9299539/pg_1?tag=artBody;col1
Composition of the essential oils and extracts of two populations of Cannabis sativa L. ssp. spontanea from Austria
Novak, Johannes

Abstract

The essential oil and the solvent extract of two populations of Cannabis sativa L. ssp. spontanea growing wild in Austria were analyzed comparatively. In the essential oil, myrcene (31% and 27%, respectively), (E)-beta-ocimene (13% and 3%, respectively) and beta-caryophyllene (11 % and 16%, respectively) were found, while in the solvent extract the non-hallucinogeneous cannabidiol (77% and 59%, respectively) dominated. The hallucinogeneous delta-9-tetrahydrocannabinol (THC) was also found in the solvent extract at a level of less than 1%.

The Plant

In Cannabis sativa L. ssp. spontanea (formerly Cannabis ruderalis) (Cannabaceae) the perianth of the female flowers is in contrast to C. sativa ssp. sativa still present; the fruit is brownish and has a peduncle-like ringbulge. It is a ruderal, but a rare plant in the east of Austria (1).

Source

Two populations of C. sativa L. ssp. spontanea ("Albrechtsfeld" and "Schoschtolacke") from the region of lake Neusiedl, Burgenland, eastern Austria were sampled in June, 1998, at the beginning of seed ripening. At each population upper parts of approximately 10 plants were sampled. Voucher specimens were deposited in the Herbarium of the Institute for Applied Botany, University of Veterinary Medicine, Vienna.

Plant Part

For distillation and extraction, only fresh material was used, since drying results in a high loss (30-40%) of the essential oil (2). Twenty g of fresh plant material (upper plant parts) were distilled in a modified Clevenger apparatus for 3 h. The solvent extracts were prepared by adding CH^sub 2^Cl^sub 2^ to 1 g fresh material of hemp (upper plant parts); extraction was performed in an ultrasonic bath for 15 min.

The essential oil (5 (mu)L) was diluted with CH^sub 2^Cl^sub 2^ (495 (mu)L) prior to analyses. GC/MS-analyses were performed on a HP 6890 coupled with a HP 5972 MSD and fitted with a HP 30 m x 0.25 mm capillary column coated with HP-5MS (0.25 (mu)m film thickness). The analytical conditions were: carrier gas helium, injector temperature 250 deg C, split ratio 50:1, temperature programme 50 deg -140 deg C at 5 deg C/min and 140-170 deg C at 2 deg C/min. Components were identified by comparing their retention indices (RI) and mass spectra (3-5).

Previous Work

The essential oil of C. sativa has been the subject of previous studies (2, 6-15 and references cited therein).

Present Work

Mono- and sesquiterpenes: The oil of C. sativa L. ssp. spontanea contains as main compounds alpha-pinene (9% and 6%, respectively), myrcene (32% and 28%, respectively), beta-- caryophyllene (11% and 16%, respectively) and beta-caryophyllene oxide (7% and 8%, respectively) (Table I). However, the main differences between the two populations could be found in the high content of (E)-beta-ocimene with a very high content of 12.6% from "Albrechtsfeld" and a low content of 3% from "Schoschtolacke." Compared to "Schoschtolacke," the content of alpha-humulene was approximately the half at "Albrechtsfeld" (3.2%).

The oil compositions reported here differ very much from Ross et al. (2), Hendriks et al. (8) and Nigam et al. (13), where (E)-beta-ocimene was only found in traces or not at all. Hendriks et al. (8) and Nigam et al. (13) found alpha-pinene, beta-- pinene and myrcene at alevel of less than 1%, beta-caryophyllene instead reached 37% and 45%, respectively. In contrast, Ross et al. (2) noticed beta-caryophyllene to be present at only 1.3%. Myrcene (67%) and limonene (16%) were much higher than reported elsewhere (2). The Austrian populations of this report are within the range of (12) where different cultivars (especially European fiber cultivars) were analyzed.

Composition of cannabinoids: Regarding the cannabinoids in the oil, relatively high percentages of the non-- hallucinogeneous cannabidiol (CBD) (9.8% "Albrechtsfeld" and 10.9% "Schoschtolacke," respectively) could be found. The hallucinogenic delta-9-tetrahydrocannabinol (THC) was only present at "Schoschtolacke," and here only at low amounts (0.7%). CBD in the oil was still very high, but it's content was strictly dependant on the distillation conditions. The presence of cannabinoids in oils at higher amounts (11,17 and this report) as well as the almost absence of cannabinoids (12 and 16) are also dependant on distillation conditions and the state of the plant material being distilled. In the solvent extract, the content of CBD was extremely high (76.6% and 58.8%, respectively), while THC was always (even in the extract) below 1%. These can be regarded as being populations with a low content of THC, while the amount of CBD (especially in the extracts) was very high. So the ratio of CBD/THC, which is used for characterizing and distinguishing "fiber" from "drug" genotypes (18), is very much in favor of the fiber types.

Alkanes: Hendriks et al. (19) found nonacosane as main compound in the alkane-fraction obtained by extraction (55%) and at 11% in the oil. Nonacosane was also detected in the extracts of our study at 9% ("Albrechtsfeld") and 18% ("Schoschtolacke"), while it was absent in the oil (Table I).

References

1. W. Adler, K. Oswald, and R. Fischer, Exkursionsflora von Osterreich. p365, Eugen Ulmer, Stuttgart, (1994).

2. S. A. Ross and M. A. ElSohly, The volatile oil composition of fresh and air-dried buds of Cannabis saliva, J. Nat. Prod., 59, 49-51 (1996).

3. R. P. Adams, Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Allured Publishing Corporation, Carol Stream, Illinois (1995).

4. F. W. McLafferty, Wiley Registry of Mass Spectral Data. John Wiley & Sons, Inc. New York (1989).

5. T. Mills III. and J. C. Roberson, Instrumental Data for Drug Analysis. Elsevier, Amsterdam (1987).

6. G. Fournier and M. R. Paris, Variabffite de la composition chimique de I'huile essentielle de Chanvre (Cannabis saliva Linnaeus). Rivista Ital. EPPOS, 60, 504-510 (1978).

7. H. Hendriks and A. P. Bruins, A tentative identification of components in the essential oil of Cannabis saliva L. by a combination of gas chromatography negative ion chemical ionization mass spectrometry and retention indices. Biomed. Mass Spectrom., 10, 377-381 (1983).

8. H. Hendriks, Th. M. Malingre, S. Batterman, and R. Bos, Mono- and sesqui-terpene hydrocarbons of the essential oil of Cannabis saliva, Phytochemistry, 14, 814-815 (1975).

9. L. Hanua, The presentstate of knowledge in the chemistry of substances of Cannabis saliva L. III. Terpenoid substances, Acta Universitatis Palackianae Olomucensis, 73, 233-239 (1975).

10. L Lemberkovics, P. Veszki, G. Verzar-Petri and A. Trka, Study on sesquiterpenes of the essential oil in the inflorescence and leaves of Cannabis saliva L. var. Mexico. Sci. Pharm., 49, 401-408 (1981).

11. Th. Malingre, H. Hendriks, S. Batterman, R. Bos and J. Visser, The essential oil of Cannabis sativa, Planta med. 28, 56-61 (1975).

12. V. Mediavilla, and S. Steinemann, Essential oil of Cannabis saliva L. strains, J, Internet. Hemp Assoc., 4, 82-84 (1997).

13. MC. Nigam, K. L. Handa, I. C. Nigam, K. L. Levi, Essential oils and their constituents. XXIX. The essential oil of marihuana: composition of genuine Indian Cannabis saliva L., Can. J. Chem., 43, 3372-3376 (1965).

14. M. Paris, L'essence de Cannabis: parfum mysterieux, Rivista Ital. EPPOS, 57, 83-86 (1975).

15. E. Stahl and R. Kunde, Neue Inhaltsstoffe aus dem atherischen 01 von Cannabis saliva, Tetrahedron Lett., 30, 2841-2844 (1973).

16. J. Novak, K. Zitterl-Egiseer, S.G. Deans and Ch. Franz, Essential oils of

different cultivars of Cannabis saliva L. and their antimicrobial activity, Flav. Fragr. J., 16, 259-262 (2001).

17. Th. Malingre, H. Hendriks, S. Batterman and R. Bos, The presence of cannabinoid components in the essential oil of Cannabis saliva L., Pharm. Weekbl., 108, 549-552 (1973),

18. I. Bocsa, and M. Kraus, Der Hanlanbau. Botanik, Sorten, Anbau and Emte. C.F.Miller, Heidelberg (1997).

19. H. Hendriks, Th. Malingre, S. Batterman and R. Bos, Alkanes of the essential oil of Cannabis saliva, Phytochemistry, 16, 719-721 (1977).

Johannes Novak* and Chlodwig Franz

Institute for Applied Botany, University of Veterinary Medicine, Veterinarplatz 1, A-1210 Wien, Austria

Copyright Allured Publishing Corporation May/Jun 2003

c-ray

09-26-2008, 05:07 PM

from http://www.ingentaconnect.com/content/bsc/boj/2005/00000147/00000004/art00001;jsessionid=3pdf3jcn2vbu8.alice?format=pri nt
[QUOTE]Cannabis sativa: volatile compounds from pollen and entire male and female plants of two variants, Northern Lights and Hawaian Indica

Authors: ROTHSCHILD, MIRIAM; BERGSTR

c-ray

09-26-2008, 05:11 PM

from http://cat.inist.fr/?aModele=afficheN&cpsidt=1087795
[QUOTE]Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity

NOVAK Johannes (1) ; ZITTERL-EGISEER Karin (1) ; DEANS Stanley G. (2) ; FRANZ Chlodwig M. (1) ;
(1) Institute for Applied Botany, University of Veterinary Medicine, Veterin

guest

09-26-2008, 05:16 PM

:clap::headbang::clap:
Dude, you fookin rock the house down.
I am sure we will have fun researching and identifying the properties of each of them.
Blessed!
:rollj::pimp:

c-ray

09-26-2008, 05:50 PM

yes I....this is going to be fun 4 sure

from http://www.hempreport.com/issues/14/farm14.html#composition
Hemp Essential Oil: Sweet Smell of Success
By Dr. Sumach

Early test offerings of industrial hemp essence from GEN-X Research (Regina, Saskatchewan) are rather wonderful. Here is the captured soul dew of a living hemp meadow under big clear sunny skies, fifty pounds of fresh hemp buds reduced to a single ounce of hemp essential oil. The initial sensation of freshness is astounding

Introducing a new aromatic to the world is like discovering a new planet or finding gold on vacation. It is a lot of work to make hemp essence; an acre of hemp yields just 3 to 5 litres of essence at an extraction rate of 0.15 % -- a mere fraction of one percent. Pure certified organic aromatic motherboard hemp essence is expensive -- $2,000 US per litre -- but this anoints a lot of product.

Swiss Hemp farmers began distilling hemp essence almost a decade ago which they calculated as the best return for their high altitude hemp crops. Their people developed an instant niche providing essence for hardcore European manufacturers of Euro hanf /chanvre perfumes, toiletries, and confections. But there is never enough hemp essence to go around.

GEN-X Research contracted a local distiller to produce hemp essential oils under (Health Canada) license -- the first in Canada. GEN-X uses their own licensed hemp. Have investigated terpene test patterns of many different hemp varieties for essential potential, they are preparing to tap the vacant hemp essence niche in North America.

As noted in our previous stories on hemp-content alcohols, there are many similarities in the organic chemistry of cannabis and hops. Both plants contain notable levels of the terpene Micron -- source of their respective characteristic odours. Myrcene appears in much lower concentrations in Juniper berries (an ingredient in Gin) and Frankincense resin (gift to baby Jesus). Recent studies suggest Myrcene has powerful antioxidant properties, and may have important health benefits.

Hemp yields a fraction of 1-% essential oil from the flowers, about the same as hops. It is more efficient to grow and distil a ton of hemp than a ton of hops. Hemp essence has other charms than just smelling nice, it is a mountain of 58 monoterpines and some 38 known sesquiterpines. Destroyed by the process of steam distillation, THC does not pass into the essence. (For composition analysis, click here)
(http://www.hempreport.com/issues/14/OilConstituentreport.html)
Folk tales that tell us that the smell of hemp discourages flies and mosquitoes is rooted in fact -- Limonene, a pleasant smelling citrus-like component in hemp essence is known to be an effective insect repellent, it is not a poison. Limonene is also a potent natural fungicide with a mild antiseptic action. It has a very pleasant smell and is very safe.

and http://www.hempreport.com/issues/14/OilConstituentreport.html
Hemp Essential Oil Analysis Report
Courtesy of: Gen-X Research Regina, Sk.
(Date received: Sept. 27, 2000)

Oil Constituent|Lot "A"|Lot "B"
percent values|"FIN-314 hemp"|"Fasamo hemp"
Myrcene|38.2|40.1
α-Terpinolene|22.2|26.6
trans-Ocimene|20.4|4.1
α-Pinene|6.6|4.2
β-Pinene|1.8|1.4
Limonene|1.2|1.7
β-Phellandrene|0.6|0.4
cis-Ocimene|0.2|0.4
Δ3-Carene|0.1|0.1
Total Monoterpenes|91.3|78.9
trans-Caryophyllene|5.0|9.8
α-Humulene|0.7|2.1
β-Farnesene|0.6|2.0
β-Selinene|0.6|0.5
Caryophyllene oxide|0.5|2.9
Phtalic acid diethyl ester|0.5|2.7
Selina-3,7(11)-diene|0.5|0.7
α-Bergamotene|0.5|0.6
Total Sesquiterpenes|8.9|21.2

Cannabinoid Content||
parts per million (PPM)|Lot "A"|Lot "B"
Δ9THC|less than 1|less than 1
CBN|less than 1|less than 1
CBD|405|595

c-ray

09-26-2008, 06:01 PM

from http://www.internationalhempassociation.org/jiha/jiha4208.html
[QUOTE]Essential oil of Cannabis sativa L. strains

Vito Mediavilla and Simon Steinemann

Swiss Federal Research Station for Agroecology and Agriculture, Reckenholzstrasse 191, 8046 Zurich, Switzerland
(E-mail: vito.mediavilla@fal.admin.ch http://www.admin.ch/sar/fal/).

Mediavilla, Vito and Simon Steinemann 1997. Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association 4(2): 80 - 82. The aroma of hemp (Cannabis sativa L.) could be of considerable commercial value if evaluation of varieties and development of extraction methods led to a pleasing scent in the resulting essential oils. We compared the composition and smell of some fiber hemp and drug Cannabis essential oils isolated by steam distillation. The essential oil of some hemp strains contained particular monoterpenes and sesquiterpenes that imparted to the specimen a desireable scent. These preliminary one-year results do not take into account the influence that harvest time and the weather "just-before-harvest" could have on the quality of the essential oil. The Δ9-tetrahydrocannabinol (THC) concentration in the essential oils was very low and varied between 0.02% and 0.08%. The ratio of this compound to cannabidiol showed only small changes during steam distillation.

Introduction

The Cannabis smell is a peculiarity of this plant. Its aroma does not originate from the terpenophenolic cannabinoids, but from the more volatile monoterpenes and sesquiterpenes (Lehmann 1995). Hashish detection dogs, for example, do not smell Δ9-tetrahydrocannabinol (THC) but are able to smell the sesquiterpene caryophyllene oxide (Stahl and Kunde 1973). According to Turner et al. (1980) 58 monoterpenes and 38 sesquiterpenes have been identified in hemp. Using steam distillation, it is possible to concentrate most of these components to an essential oil.

Many utilizations for hemp essential oil are known. They impart the typical Cannabis aroma to such products as cosmetics, soaps, shampoos, creams, oils, perfumes and also to foodstuffs. Additional possible uses are for aroma therapy and as a means for plant protection. According to McPartland (1997), two essential hemp oil components (limonene and alpha-pinene) have a repellent effect against many insects. The bacteriostatic activity of hemp essential oil has been reported by Fournier et al. (1978). Although first trials of hemp essential oil used against potato late blight (Phytophthora infestans) were not promising (Krebs 1996), cannabinoid antifungal activity cannot be discounted.

The aim of the work presented here was to assess the variability of hemp essential oil from different Cannabis strains.

Materials and methods

Fiber and drug cultivars (Tab. 1) were grown in 1996 near Zurich, Switzerland (approximately 47

Green Supreme

09-26-2008, 07:36 PM

Go C go. Its gonna take me a week to digest that. Peace GS

c-ray

09-27-2008, 01:25 AM

Loki

09-27-2008, 05:33 AM

So, if all these compounds can be identified, isolated and extracted, we could have custom blended weed aromas. That would be very cool.

The Cannarchist

09-27-2008, 06:56 AM

Strangely enough.......:muahaha:

There is a market for cannibinoid terpenes in the perfume industry.

Eau de Cannabis anybody?

One plant this year I just wanted to roll in....:D

c-ray

09-27-2008, 07:19 AM

perfumes are thc free so....just need a place to grow all those plants
50lbs of bud to make 1 ounce of essential oil
10000 plants per hectare @ 1 plant per square metre = roughly 10000 lbs or 200 ounce of essential oil which could be worth say $200 an ounce or about $8 a ml at the retail end...so incomes of $10,000+ per hectare for the farmer are entirely possible
one limitation would be the amount of material that one could process on a daily basis, if it were possible to process fresh material maybe using low pressure co2..otherwise plants could be dried to a certain level and stored and processed over the winter
a co2 extractor would be pretty key I'd imagine, and it would be possible to figure out the size of the extractor that is needed based on how much acreage is sown

Nirrity

09-29-2008, 06:21 PM

Always wondering does anything get losted during water bubblehash extraction...

Greens

10-04-2008, 12:32 AM

Great thread, c-ray.

I'm a real limonene and pinene FREAK! Also, whatever makes that sweet seasoning meaty smell in the GG is awesome too (myrcene?).

I am convinced that terpenes/terpenoids play a role in the type of high resulting from different strains of herb.

Skunky strains are always stupifying.

Lemony strains deliver a soaring, uplifting high with fast onset.

Perfumy strains are also uplifting, but not quite as noticeable.

Berry smelling strains are relaxing and mellow.

Piney strains are heavy and stupifying.

Sour grape mixed with black licorice strains are usually quite couchy, but euphoric.

Meaty/seasoning strains are very euphoric and are long lasting (usually creeper too).

Musky/spicy strains tend to be very energetic and can get the heart going.

Of course, there are exceptions to these. I mean, a piney strain that has very little THC is not going to be very heavy. Also, these smells are often mixed together in the same strain, resulting in very complex highs.

Greens

TGAbadboy

10-16-2008, 04:43 PM

Very awesome Thread Bring on the K smelling perfume... Big ups Cray...

c-ray

10-29-2008, 01:30 PM

this could be useful

jefbzh

10-29-2008, 01:40 PM

tks cray is good thread can i use this ?just for the vibes ?
tks again
jef

Monseigneur Stroganoff

10-29-2008, 03:39 PM

thankyou c-ray!!

Green Supreme

09-21-2009, 02:18 AM

The Volatile Oil Composition of Fresh and Air-Dried Buds of Cannabis sativa.
Scooped this from another site.
The Volatile Oil Composition of Fresh and Air-Dried Buds of Cannabis sativa

Link to PDF study
http://cannabis-science.com/papers/oil%20comp%20cannabis.pdf.

Samir A. Rossi and Mahmoud A. ElSohly*?'J
Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi 38677,
and Department of Pharmaceutics, School of Pharmacy, University of Mississippi, University, Mississippi 38677

Received January 12, 1995@

The composition of the steam-distilled volatile oil of fresh and air-dried, indoor-grown marijuana was studied by GC/FID and GC/MS. In all, 68 components were detected of which 57 were fully identified. Drying of the plant material had no effect on the qualitative composition of the oil and did not affect the ability of individuals familiar with marijuana smell to recognize the odor.
__________________peace GS

Alchemist

11-13-2009, 05:24 PM

hey guys, whats the yield on canna essential oils?

rose petals had the lowest yield ive seen, 0.5% w/w

mints usually have around 2-4%

liquid co2 is best for essential oils!!

great discussion!

c-ray

11-13-2009, 08:39 PM

I am guessing 1-2%

Monseigneur Stroganoff

09-07-2010, 05:18 PM

icmag

"Myrcene is the most prevalent terpene found in most varieties of marijuana but not found in hemp. It is also present in high amounts in hops, lemon grass, East Indian bay tree, verbena and the plant from which it derives its name mercia. Myrcene appears in small amounts in the essential oils of many other plants.

Its odor is variously described as clove like, earthy, green-vegatative, citrus, fruity with tropical mango and minty nuances(In fact, myrcene is found in large qauntities in cavalo, rosa, espada, and paulista mangos). The various odors are the result of slight differences in the overall esential oil makeup. All of these flavors and odors are commonly used to describe Cannabis.

Myrcene is a potent analgesic, anti-inflammatory and antibiotic. It blocks the actions of cytochrome, aflatoxin B and other pro-mutagens that are implicated in carcinogenesis. It is present in small amounts in many essential oils associated with anti-depressive and uplifting behavior.

Myrcene is probably a synergist of THC: A combination of the two molecules creates a stronger experience than THC alone. Myrcene probably affects the permiability of the cell membranes, thus it may allow more THC to reach brain cells.

LIMONENE is found in the rinds of citrus and many other fruits and flowers. It is the second, third or fourth most prevalent terpene in cannabis resins. Everyone is familiar with the odor of citrus resins. They explode into the air when a fruit is peeled. The exact order is determined by the structure of the terpene.

Limonene has anti-bacterial, anti-fungal and anti cancer activities. It inhibits the ras cancer gene cascade, which promotes tumor growth. It is used to synergistically promote the absorbtion of other terpenes by penetrating cell membranes. Limonene sprays are also used to treat depression.

Since Limonene is such a potent anti-fungal and anti-cancer agent, it is thought to protect against aspergillus fungi and carcinogens found in cannabis smoke streams
.
Plants use Limonene to repulse predators. For instance, flies have a group of receptors similar in function to the taste buds on our tongues. One of them detects noxious chemicals, and responds to Limonene as if it were toxic. This is hard wired into the flies brain.

In humans, Limonene's design facilitates a direct response by quickly permeating the blood-brain barrier. The result is increased systolic blood pressure. One test, reported subjective alertness and restlessness. Various Limonene analogs can cue the brain to sexuality, buoyancy, or focused attention.

Caryophylene is a major terpene found in black pepper(15-25%), clove(10-20%) and cotton(15-25%). It is found in smaller %'s in many other herbs, and spices. It has a sweet, woody and dry clove odor and tastes pepper spicy with camphor and astringent citrus backgrounds. It contributes to black pepper's spiciness. The oil is used industrially to enhance tobacco flavor.

Caryophylene, given in high amounts, is a calcium and potassium ion channel blocker. As a result, it impedes the pressure excerted by heart muscles. As a topical it is analgesic and is one of the active constituents that makes clove oil, a preferred treatment for toothache.
It does not seam to be involved in mood change.

Pinene is the familiar odor associated with pine trees and their resins. It is the major component in turpentine and is found in many other plant essential oils in noticeable amounts including rosemary, sage, and eucalyptus. Many additional plant oils contain pinene.

Pinene is used medically as an expectorant, and topical antiseptic. It easily crosses the blood-brain barrier where it acts as a acetylcholinesterase inhibitor; that is, it inhibits activity of a chemical that destroys an information transfer molecule. This results in better memory. Largely due to the presence of pinene, rosemary and sage are both considered "memory plants."
Concoctions made from their leaves have been used for thousands of years in traditional medicine to retain and restore memory.

Pinene probably gives true skunk varieties, the ones that stink like the animal, much of their odor. It is also a bronchodilator. The smoke seems to expand in your lungs and the high comes on very quickly since a high percentage of the substance will pass into the bloodstream and brain. It also increases focus, self satisfaction and energy, which seems counterintuitive, but for the presence of terpineol.

TERPINEOL has a lilac, citrus or apple blossom/lime odor. It is a minor constituent of many plant essential oils. It is used in perfumes and soaps for fragrance.

Terpineol is obtained commercially from processing other turpines. It reduces motillity- the capability for movement- by 45% in lab rat tests. This may account for the couchlock effects of some cannabis although that odor is not usually associated with body highs. However, Terpineol is often found in cannabis with high pinene levels. Its odor would be masked by the pungent woodsy aromas of pinene.

BORNEOL smells much like the menthol aroma of camphor and is easily converted into it. It is found in small quantities in many essential oils. Comercially it is derived from artemisia plants such as wormwood and some species of cinnamon.

It is considered a "calming sedative" in chinese medicine. It is directed for fatigue, recovery from illness and stress.

The camphor like overtones of Silver Haze varieties are unmistakable. The high does have a calming effect as well as its psychedelic aspects. This probably means there is a large amounts of borneol present.

DELTA 3-CARENE has a sweet pungent odor. It is a constituent of pine and cedar resin but is found in many other plants including rosemary. In aroma therapy, cypress oil, high in D-3-carene, is used to dry excess fluids, tears, running noses, excess menstrual flow and perspiration. It may contribute to the dry eye and mouth experienced by some marijuana users.

LINALOOL has a floral scent reminiscent of spring flowers such as lily of the valley, but with spicy overtones. It is refined from lavender, neroli, and other essential oils. Humans can detect its odor at rates as low as one part per million in the air.

Linalool is being tested now for treatment of several types of cancer. It is also a component of several sedating essential oils. In tests on humans who inhaled it, it caused severe sedation. In tests on lab rats it reduced there activity by almost 75%.

PULEGONE has a minty-camphor odor and flavor that is used in the candy industry. It is implicated in liver damage in very high dosages. It is found in tiny quantities in marijuana.

Pulegone is an acetylcholinesterase inhibitor. That is, it stops the action of the protein that destroys acetylcholine, which is used by the brain to store memories. It may counteract THC's activity, which leads to low acetylcholine levels. The result is you would forget more on THC alone than THC accompanied by pulegone.

1,8-CINEOLE is the main ingredient in oil of eucalyptus. It has camphor-minty odor. It is also found in other fragrant plants and in minor amounts in marijuana. It is used to increase circulation, pain relief and has other topical uses.

Cineole easily crosses the blood-brain-barrier and triggers a fast olfactory reaction. Eucalyptus oil is considered centering, balancing and stimulating. It is probably the stimulating and thought provoking part of the cannabis smoke stream."

Green Supreme

09-09-2010, 05:23 AM

More from IC mag

This is what Sam wrote to the Society of Cannabis Clinicians:

"To the Society of Cannabis Clinicians:
Most interesting to me are the modulating effects of the 120
Terpenoids found in Cannabis. Pure THC is pretty boring, flat, one dimensional with little individuality. Not sure I would be a Cannabis smoker if THC was all there was. But add a small amount of Terpenoids and the picture changes, some Terpenoids like Limonene make the subjective high much faster in onset and much stronger, with rushes, more clear, speedy, up, cerebral, euphoric, psychedelic. While other
Terpenoids like Myrcene make the THC physical, mellow, sleepy, as well as stronger.
It has been obvious to me for more then 20 years that Terpenoids played a major role in modulating the effects of THC, but now for the first time I have proof. I did the work with a volcano, using liquid pads for putting the Cannabinoids/Terpenoids on, and used Cannabinoids that were 99%+ purity.
I tried pure THC, THCV, CBD, CBN, CBG, and CBC will be next, I have gram+ amounts of each. I have also tried a dozen pure Terpenoids with and without Cannabinoids. I used the Musty drug reaction scale before and after dosing as well as a better more specific one designed by myself for all of the tastes, smells and effects of the Terpenoid/Cannabinoid
inter-reactions. I have 10 subjects so far doing the testing with me.
The bottom line is that all of the reported different effects of
different varieties of Cannabis are reputed to be from the
Cannabinoids. But besides the effects from THC and very occasional small amounts of CBD found in herbal Cannabis, all of the different reported subjective effects are in fact from the Terpenoids/THC. This has to be good news for proponents of herbal Cannabis over pure THC for medicine? I do not know if the Terpenoids are as active in modulating THC if the dose is oral by eating."

Peace GS