Flashcards: Terpenes and terpenoids

Sclareol is a fragrant chemical compound found in clary sage (Salvia sclarea), from which it derives its name.

Squalane is a hydrocarbon and triterpene derived by hydrogenation of squalene.

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.

Abietic acid (also known as abietinic acid or sylvic acid) is an organic compound that occurs widely in trees.

Natural rubber, also called India rubber or caoutchouc, as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds plus water.

Eucalyptol is a natural organic compound that is a colorless liquid.

Tinyatoxin (TTX or TTN) is a highly irritant analog of resiniferatoxin and capsaicin.

Plastoquinone (PQ) is a quinone molecule involved in the electron transport chain in the light-dependent reactions of photosynthesis.

Tetrahydrocannabinol (THC, dronabinol by INN), or more precisely its main isomer (−)-trans-Δ9-tetrahydrocannabinol, is the principal psychoactive constituent (or cannabinoid) of cannabis.

The term carotene (also carotin, from the Latin carota, "carrot") is used for many related unsaturated hydrocarbon substances having the formula C40Hx, which are synthesized by plants but in general cannot be made by animals (with the sole known exception of some aphids and spider mites which acquired the synthetic genes from fungi).

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C═C double bonds, two of them being triply substituted and one being doubly substituted.

Piperitone is a natural monoterpene ketone which is a component of some essential oils.

β-Santalol is an organic compound that is classified as a sesquiterpene.

Limonene is a colorless liquid hydrocarbon classified as a cyclic terpene.

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.

Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives.

Menthol is an organic compound or obtained from corn mint, peppermint, or other mint oils.

Geraniol is a monoterpenoid and an alcohol.

Linalool (/lᵻˈnæloʊˌɒl, liː-, -loʊˌɔːl, -ləˌwɒl, -ləˌwoʊl/ or /ˌlɪnəˈluːl/) is a naturally occurring terpene alcohol chemical found in many flowers and spice plants with many commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness).

Cantharidin is an odorless, colorless terpenoid secreted by many species of blister beetles, including broadly in genus Epicauta, and in species Lytta vesicatoria (Spanish fly).

Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either a pair, or a mixture of terpenoids with the molecular formula C10H16O.

Borneol is a bicyclic organic compound and a terpene.

Ocimenes are a group of isomeric hydrocarbons.

Citronellal or rhodinal or 3,7-dimethyloct-6-en-1-al (C10H18O) is a monoterpenoid, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans.

Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal.

Nepetalactone is an organic compound, first isolated from the plant catnip (Nepeta cataria), which acts as a cat attractant.

Cadinene is the trivial chemical name of a number of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants.

Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties.

Fenchone is a natural organic compound classified as a monoterpene and a ketone.

Nerol is a monoterpene found in many essential oils such as lemongrass and hops.

Nerolidol, also known as peruviol, is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers.

Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1.

Terpinen-4-ol, also known as 4-Terpineol, is an organic compound in the terpene family.

Camphene is a bicyclic monoterpene.

Carvone is a member of a family of chemicals called terpenoids.

Pimaric acid is a carboxylic acid from the resin acid group.

Fenchol or 1,3,3-trimethyl-2-norbornanol is a terpene and an isomer of borneol.

Nootkatone is a natural organic compound and is the most important and expensive aromatic of grapefruit.

Jasmone is an organic compound, which is a volatile portion of the oil from jasmine flowers.

Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid.

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes.

Betulin (lup-20(29)-ene-3β,28-diol) is an abundant, naturally occurring triterpene.

Isopimaric acid (IPA) is a toxin which acts as a large conductance Ca2+-activated K+ channel (BK channel) opener.

Turpentine (also called spirit of turpentine, oil of turpentine, wood turpentine and colloquially turps) is a fluid obtained by the distillation of resin obtained from live trees, mainly pines.

Carvacrol, or cymophenol, C6H3CH3(OH)(C3H7), is a monoterpenoid phenol.

Menthyl acetate is a natural monoterpene which contributes to the smell and flavor of peppermint.

Linalyl acetate is a naturally occurring phytochemical found in many flowers and spice plants.

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria.

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol.

The ionones are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones.

Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil.

Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants.

Thujone (/ˈθuːdʒoʊn/) is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (−)-α-thujone and (+)-β-thujone.

Resin acid refers to mixtures of several related carboxylic acids, primarily abietic acid, found in tree resins.

The terpinenes are a group of isomeric hydrocarbons that are classified as terpenes.

Menthone is a naturally occurring organic compound with a molecular formula C10H18O.

Geranyl acetate is a natural organic compound that is classified as a monoterpene.

Lavandulol is a monoterpene alcohol found in a variety of essential oils such as lavender oil.

Polyprenols are natural long-chain isoprenoid alcohols of the general formula H-(C5H8)n-OH where n is the number of isoprene units.

Teprenone (or geranylgeranylacetone) is a pharmaceutical drug used for the treatment of gastric ulcers.

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds.

Camphor (/ˈkæmfər/) is a waxy, flammable, white or transparent solid with a strong aroma.

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants.

Geranylfarnesyl pyrophosphate is an intermediate used by organisms in the biosynthesis of sesterterpenoids.

Bactoprenol is a lipid synthesized by three different species of lactobacilli.

Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea.

Dolichol refers to any of a group of long-chain mostly unsaturated organic compounds that are made up of varying numbers of isoprene units terminating in an α-saturated isoprenoid group, containing an alcohol functional group.

Humulone (α-lupulic acid), a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops (Humulus lupulus).

Perillyl alcohol (IUPAC name: [4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol) and its precursor limonene are naturally occurring monocyclic terpenes derived from the mevalonate pathway in plants.

Rotundone is a sesquiterpene originally discovered in the tubers of cyperus rotundus.

Sterpuric acid is a phytotoxic metabolite derived from the fungus Stereum purpureum, from which it derives its name.

Methyllycaconitine (MLA) is a diterpenoid alkaloid found in many species of Delphinium (larkspurs).

Luteone is a twenty-three carbon terpenoid from a sea slug, the dorid nudibranch Cadlina luteomarginata.

C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate), also known as bactoprenol, is an essential molecule involved in construction of the bacterial peptidoglycan cell wall.

Callicarpenal is a terpenoid that has been isolated from plants of the genus Callicarpa (beautyberry).

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is an experimental antitumor agent.