Olivetol
Encyclopedia
Olivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen
; it is also a precursor
in various syntheses of tetrahydrocannabinol
.
s and can be readily extracted.
The cannabis
plant also internally produces the related substance olivetolic acid, which it in turn uses to biosynthesize the psychoactive product tetrahydrocannabinol
(THC).
s, which can produce a synthetic form of THC.
One such method is a condensation reaction of olivetol and pulegone
as mentioned in the book PiHKAL
by Alexander Shulgin
. In PiHKAL, Shulgin also notes a cruder method of producing the same product by bringing to reaction olivetol and the essential oil
obtained from orange
peel in the presence of phosphoryl chloride
. It can also be produced by reacting olivetol with a-pinene.
Another method for the stereospecific synthesis of Δ9-tetrahydrocannabinol comprising condensing olivetol with 2-carene
oxide.
Lichen
Lichens are composite organisms consisting of a symbiotic organism composed of a fungus with a photosynthetic partner , usually either a green alga or cyanobacterium...
; it is also a precursor
Precursor (chemistry)
In chemistry, a precursor is a compound that participates in the chemical reaction that produces another compound. In biochemistry, the term "precursor" is used more specifically to refer to a chemical compound preceding another in a metabolic pathway....
in various syntheses of tetrahydrocannabinol
Tetrahydrocannabinol
Tetrahydrocannabinol , also known as delta-9-tetrahydrocannabinol , Δ1-THC , or dronabinol, is the main chemical psychoactive substance found in the cannabis plant. It was first isolated in 1964. In pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed...
.
Occurrence
Olivetol is a naturally occurring organic compound. It is found in certain species of lichenLichen
Lichens are composite organisms consisting of a symbiotic organism composed of a fungus with a photosynthetic partner , usually either a green alga or cyanobacterium...
s and can be readily extracted.
The cannabis
Cannabis
Cannabis is a genus of flowering plants that includes three putative species, Cannabis sativa, Cannabis indica, and Cannabis ruderalis. These three taxa are indigenous to Central Asia, and South Asia. Cannabis has long been used for fibre , for seed and seed oils, for medicinal purposes, and as a...
plant also internally produces the related substance olivetolic acid, which it in turn uses to biosynthesize the psychoactive product tetrahydrocannabinol
Tetrahydrocannabinol
Tetrahydrocannabinol , also known as delta-9-tetrahydrocannabinol , Δ1-THC , or dronabinol, is the main chemical psychoactive substance found in the cannabis plant. It was first isolated in 1964. In pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed...
(THC).
Synthesis of Products
This compound has been documented as being a usable ingredient in various methods of condensation reactionCondensation reaction
A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...
s, which can produce a synthetic form of THC.
One such method is a condensation reaction of olivetol and pulegone
Pulegone
Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria , Mentha piperita, and pennyroyal. It is classified as a monoterpene....
as mentioned in the book PiHKAL
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
. In PiHKAL, Shulgin also notes a cruder method of producing the same product by bringing to reaction olivetol and the essential oil
Essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
obtained from orange
Orange (fruit)
An orange—specifically, the sweet orange—is the citrus Citrus × sinensis and its fruit. It is the most commonly grown tree fruit in the world....
peel in the presence of phosphoryl chloride
Phosphoryl chloride
Phosphoryl chloride is a colourless liquid with the formula 3. It hydrolyses in moist air to phosphoric acid to release choking fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide...
. It can also be produced by reacting olivetol with a-pinene.
Another method for the stereospecific synthesis of Δ9-tetrahydrocannabinol comprising condensing olivetol with 2-carene
Carene
Carene, or delta-3-carene, is a bicyclic monoterpene which occurs naturally as a constituent of turpentine, with a content as high as 42% depending on the source. Carene has a sweet and pungent odor. It is not soluble in water, but miscible with fats and oils....
oxide.