Names | |
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IUPAC name (1R,2R,4aS,8aS)-1-{(3E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol | |
Other names Ambrein | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.006.784 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C30H52O | |
Molar mass | 428.745 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. [1] Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.
It has been shown to act as an analgesic [2] and has been proven to increase sexual behavior in rats, [3] providing some support for its traditional aphrodisiac use.
Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It reduces these contractions by serving as an antagonist and interfering with Ca2+ ions from outside the cell. [4]
In 1946, Ruzicka and Lardon "established that the fragrance of ambergris is based on the triterpene (named) ambrein". [5] [6] [7]
Ambrein is synthesized from the common triterpenoid precursor squalene. The squalene-hopene cyclase (SHC) catalyzes the cyclization of squalene into the monocyclic 3-deoxyachilleol A. Tetraprenyl-beta-curcumene synthase (BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein. [8]
Ambergris, ambergrease, or grey amber is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a marine, fecal odor. It acquires a sweet, earthy scent as it ages, commonly likened to the fragrance of isopropyl alcohol without the vaporous chemical astringency.
An aphrodisiac is a substance alleged to increase libido, sexual desire, sexual attraction, sexual pleasure, or sexual behavior. These substances range from a variety of plants, spices, and foods to synthetic chemicals. Natural aphrodisiacs, such as cannabis or cocaine, are classified into plant-based and non-plant-based substances. Synthetic aphrodisiacs include MDMA and methamphetamine. Aphrodisiacs can be classified by their type of effects. Aphrodisiacs that contain hallucinogenic properties, such as bufotenin, have psychological effects that can increase sexual desire and sexual pleasure. Aphrodisiacs that have smooth muscle relaxing properties, such as yohimbine, have physiological effects that can affect hormone concentrations and increase blood flow.
A steroid is an organic compound with four fused rings arranged in a specific molecular configuration.
Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.
The cremaster muscle is a paired structure made of thin layers of striated and smooth muscle that covers the testicles and the spermatic cords in human males. It consists of the lateral and medial parts. Cremaster is an involuntary muscle, responsible for the cremasteric reflex; a protective and physiologic superficial reflex of the testicles. The reflex raises and lowers the testicles in order to keep them protected. Along with the dartos muscle of the scrotum, it regulates testicular temperature, thus aiding the process of spermatogenesis.
Leopold Ružička was a Croatian-Swiss scientist and joint winner of the 1939 Nobel Prize in Chemistry "for his work on polymethylenes and higher terpenes" "including the first chemical synthesis of male sex hormones." He worked most of his life in Switzerland, and received eight doctorates honoris causa in science, medicine, and law; seven prizes and medals; and twenty-four honorary memberships in chemical, biochemical, and other scientific societies.
Uterine contractions are muscle contractions of the uterine smooth muscle that can occur at various intensities in both the non-pregnant and pregnant uterine state. The non-pregnant uterus undergoes small, spontaneous contractions in addition to stronger, coordinated contractions during the menstrual cycle and orgasm. Throughout gestation, the uterus enters a state of uterine quiescence due to various neural and hormonal changes. During this state, the uterus undergoes little to no contractions, though spontaneous contractions still occur for the uterine myocyte cells to experience hypertrophy. The pregnant uterus only contracts strongly during orgasms, labour, and in the postpartum stage to return to its natural size.
Yohimbine, also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. Yohimbine is an α2-adrenergic receptor antagonist, and has been used in a variety of research projects. It is a veterinary drug used to reverse sedation in dogs and deer.
Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as Squalus is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection.
Hopanoids are a diverse subclass of triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of pentacyclic molecules therefore refers to simple hopenes, hopanols and hopanes, but also to extensively functionalized derivatives such as bacteriohopanepolyols (BHPs) and hopanoids covalently attached to lipid A.
Not to be confused with the Croatian city of Knin
Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.
Calciseptine (CaS) is a natural neurotoxin isolated from the black mamba Dendroaspis p. polylepis venom. This toxin consists of 60 amino acids with four disulfide bonds. Calciseptine specifically blocks L-type calcium channels, but not other voltage-dependent Ca2+ channels such as N-type and T-type channels.
Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.
Muscle is a soft tissue, one of the four basic types of animal tissue. There are three types of muscle tissue in vertebrates: skeletal muscle, cardiac muscle, and smooth muscle. Muscle tissue gives skeletal muscles the ability to contract. Muscle tissue contains special contractile proteins called actin and myosin which interact to cause movement. Among many other muscle proteins, present are two regulatory proteins, troponin and tropomyosin. Muscle is formed during embryonic development, in a process known as myogenesis.
Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.
Ejaculation is the discharge of semen from the penis through the urethra. It is the final stage and natural objective of male sexual stimulation, and an essential component of natural conception. After forming an erection, many men emit pre-ejaculatory fluid during stimulation prior to ejaculating. Ejaculation involves involuntary contractions of the pelvic floor and is normally linked with orgasm. It is a normal part of male human sexual development.
Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.
The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton), and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.
Diplopterol is a triterpenoid molecule commonly produced by bacteria, ferns, and a few protozoans. This compound, classified as a member of the hopanoid family, is synthesized from triterpenoid precursor squalene. It is generally believed that hopanoids serve a similar function in bacteria as that of sterols in eukaryotes, which involves modulating membrane fluidity. Diplopterol serves as a useful biomarker for prokaryotic life, along with oxygen content at the time of sediment deposition.