Elemicin is a phenylpropene, a natural

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, and is a constituent of several plant species'

essential oils An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

Natural occurrence

Elemicin is a constituent of the

oleoresin Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvents used for their production. The oleoresin of conifers is known as crude turpentine or gum turpentine, which consists of oil o ...

and the essential oil of '' Canarium luzonicum'' (also referred to as elemi). Elemicin is named after this tree. One study found it to compose 2.4% of the fresh essential oil. Elemicin is also present in the oils of the spices

nutmeg Nutmeg is the seed, or the ground spice derived from the seed, of several tree species of the genus '' Myristica''; fragrant nutmeg or true nutmeg ('' M. fragrans'') is a dark-leaved evergreen tree cultivated for two spices derived from its fru ...

and mace, with it composing 2.4% and 10.5% of those oils respectively. Structurally, elemicin is similar to myristicin, differing only by myristicin's methyl group that joins the two oxygen atoms that make up its dioxymethy moiety, with both constituents being found in nutmeg and mace.

Isolation

Elemicin was first isolated from elemi oil using vacuum distillation. Specifically, the substance was collected between 162-165 °C at a reduced pressure of 10

torr The torr (symbol: Torr) is a Pressure#Units, unit of pressure based on an absolute scale, defined as exactly of a standard atmosphere (unit), atmosphere (101325 Pa). Thus one torr is exactly (≈ ). Historically, one torr was intended to be ...

Preparation

Elemicin has been synthesized from

syringol Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, alth ...

and allyl bromide using

Williamson ether synthesis The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ...

and

Claisen rearrangement The Claisen rearrangement is a powerful carbon–carbon chemical bond, bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl Vinyl group, vinyl ether will initiate a Sigmatropic reaction, ,3sigmatropic r ...

. The

electrophilic aromatic substitution Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic ring, aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitut ...

entering the ''para''-position was made possible by secondary Cope rearrangement. This is due to syringol's allyl

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

being blocked by ethers in both ''ortho''-positions. When blocked the allyl group migrates to the ''para''-position, in this case with yields above 85%.

Uses

Elemicin has been used to synthesize the proto-

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

Pharmacology

Raw nutmeg causes

anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the acetylcholine (ACh) neurotransmitter at synapses in the central nervous system, central and peripheral nervous system. These agents inhibit the parasympatheti ...

-like effects, which are attributed to elemicin and myristicin. Elemicin inhibits Stearoyl-CoA Desaturase 1 (SCD1) by metabolic activation. Elemicin is one of the main components in aromatic food and has antimicrobial, antioxidant, and antiviral activities. Elemicin possesses genotoxicity and carcinogenicity. Excess consumption of raw nutmeg results in delirium and disorientation. Elemicin's psychoactivity is still a point of research, however some research suggests it may act like an agonist of the 5-HT2A receptors, similar to many psychedelics. However, this is controversial as the psychoactive effects of elemicin and plants it is found in, such as nutmeg, seem to cause more

deliriant Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to th ...

-like effects than psychedelic ones.

References