Drupanol

Last updated
Drupanol
Drupanol.svg
Identifiers
  • 4-(3-Ethenyl-3,6-dimethyl-1-methylene-5-heptenyl)phenol
CAS Number
UNII
Chemical and physical data
Formula C18H24O
Molar mass 256.389 g·mol−1
3D model (JSmol)
  • CC(C)=CCC(C)(CC(=C)C1=CC=C(O)C=C1)C=C
  • InChI=1/C18H24O/c1-6-18(5,12-11-14(2)3)13-15(4)16-7-9-17(19)10-8-16/h6-11,19H,1,4,12-13H2,2-3,5H3
  • Key:CRWULAJEYWVGOC-UHFFFAOYNA-N

Drupanol is a naturally occurring phenol that has been isolated from the seeds of Psoralea drupaceae. [1] [2] Although drupanol is sometimes said to be the same compound as bakuchiol, the two compounds are in fact distinct; they have the same molecular formula and weight but different chemical structures and hence are structural isomers. [1] Bakuchiol has been found to possess antiandrogenic activity in vitro . [3]

Related Research Articles

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Creosote</span> Tar distillation byproduct used as wood preservative

Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood, or fossil fuel. They are typically used as preservatives or antiseptics.

<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

<span class="mw-page-title-main">Secondary metabolite</span> Type of organic compound

Secondary metabolites, also called specialised metabolites or secondary products, are a type of natural product generated by lifeforms that are not directly involved in the normal growth, development, or reproduction of the organism. Instead, they generally mediate ecological interactions, which may produce a selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs.

<span class="mw-page-title-main">Food browning</span> Food process

Browning is the process of food turning brown due to the chemical reactions that take place within. The process of browning is one of the chemical reactions that take place in food chemistry and represents an interesting research topic regarding health, nutrition, and food technology. Though there are many different ways food chemically changes over time, browning in particular falls into two main categories: enzymatic versus non-enzymatic browning processes.

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

<span class="mw-page-title-main">Coumarin</span> Aromatic chemical compound

Coumarin or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and considered as a lactone.

<span class="mw-page-title-main">Phenol red</span> Chemical compound

Phenol red is a pH indicator frequently used in cell biology laboratories.

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.

PubChem is a database of chemical molecules and their activities against biological assays. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH). PubChem can be accessed for free through a web user interface. Millions of compound structures and descriptive datasets can be freely downloaded via FTP. PubChem contains multiple substance descriptions and small molecules with fewer than 100 atoms and 1,000 bonds. More than 80 database vendors contribute to the growing PubChem database.

<span class="mw-page-title-main">JWH-133</span> Chemical compound

JWH-133(Dimethylbutyl-deoxy-Delta-8-THC) is a potent selective CB2 receptor agonist with a Ki of 3.4nM and selectivity of around 200x for CB2 over CB1 receptors. It was discovered by and named after, John W. Huffman.

<span class="mw-page-title-main">Hyperoside</span> Chemical compound

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

<span class="mw-page-title-main">Phenolic content in tea</span> Natural plant compounds

The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Hexamethylbenzene</span> Chemical compound

Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929, Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity.

<span class="mw-page-title-main">Atraric acid</span> Chemical compound

Atraric acid is a naturally occurring phenolic compound and ester with the IUPAC name methyl 2,4-dihydroxy-3,6-dimethylbenzoate and molecular formula C10H12O4. It occurs in the root-bark of Pygeum africanum and Evernia prunastri (Oakmoss). There is evidence to suggest that it has antiandrogenic activity in humans and its use in treatment of benign prostate hyperplasia, prostate cancer, and spinal and bulbar muscular atrophy has been investigated.

<span class="mw-page-title-main">Bakuchiol</span> Chemical compound

Bakuchiol is a meroterpenoid in the class terpenophenol.

A meroterpene is a chemical compound having a partial terpenoid structure.

<span class="mw-page-title-main">Psoralidin</span> Chemical compound

Psoralidin is a natural phenolic compound found in the seeds of Psoralea corylifolia.

The molecular formula C18H24O (molar mass: 256.39 g/mol, exact mass: 256.1827 u) may refer to:

References

  1. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 120,473. ISBN   978-1-4757-2085-3.
  2. Golovina LA, Nikonov GK (1973). "The structure of drupanol — A new phenol from Psoralea drupaceae". Chemistry of Natural Compounds. 9 (1): 7–9. doi:10.1007/BF00580876. ISSN   0009-3130. S2CID   4813778.
  3. Miao L, Ma SW, Fan GW, Wang H, Wang YF, Chai LJ (2013). "Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity". Tianjin Journal of Traditional Chinese Medicine. 5: 012.