2,4-Bis(4-hydroxybenzyl)phenol

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2,4-Bis(4-hydroxybenzyl)phenol
2,4-Bis(4-hydroxybenzyl)phenol.svg
Names
Preferred IUPAC name
4,4′-[(4-Hydroxy-1,3-phenylene)bis(methylene)]diphenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH C087793
PubChem CID
UNII
  • InChI=1S/C20H18O3/c21-18-6-1-14(2-7-18)11-16-5-10-20(23)17(13-16)12-15-3-8-19(22)9-4-15/h1-10,13,21-23H,11-12H2
    Key: YQOVRUAPWCGSLC-UHFFFAOYSA-N
  • c2cc(O)ccc2Cc1cc(ccc1O)Cc3ccc(O)cc3
Properties
C20H18O3
Molar mass 306.361 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4-Bis(4-hydroxybenzyl)phenol is a phenolic compound produced by the saprophytic orchid Gastrodia elata [1] and by the myco-heterotroph orchid Galeola faberi . [2]

Related Research Articles

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<i>Galeola</i> Genus of orchids

Galeola is a genus of orchids belonging to the subfamily Vanilloideae.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 CFR 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

<i>Gastrodia</i> Genus of orchids

Gastrodia, commonly known as potato orchids, is a genus of terrestrial leafless orchids in the family Orchidaceae, about ninety of which have been described. Orchids in this genus have fleshy, upright stems and small to medium-sized resupinate flowers with narrow sepals and petals. They are native to Asia, Australia, New Zealand, central Africa, and various islands of the Indian and Pacific Oceans.

<i>Gastrodia elata</i> Species of plant

Gastrodia elata is a saprophytic perennial herb in the family Orchidaceae. It is found in Nepal, Bhutan, India, Japan, Korea, Siberia, Taiwan, and China.

<span class="mw-page-title-main">4-Hydroxybenzaldehyde</span> Chemical compound

4-Hydroxybenzaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO). Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

<i>Armillaria nabsnona</i> Species of fungus

Armillaria nabsnona is a species of fungus in the family Physalacriaceae. The species is found in the west coast of North America, Hawaii, and Japan, where it grows on decaying hardwoods, particularly species of alder. Its fruit bodies have convex to flattened orange-brown caps up to 7 cm in diameter, brown stipes, and whitish to pinkish-tan gills.

<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">Gastrodin</span> Chemical compound

Gastrodin is a chemical compound which is the glucoside of gastrodigenin. It has been isolated from the orchid Gastrodia elata and from the rhizome of Galeola faberi. It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.

Azpeytia is a genus of hoverfly. Larvae of one species Azpeytia shirakii is known to live in the corms and stems of an orchid Gastrodia elata.

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

Chebulic acid is a phenolic compound isolated from the ripe fruits of Terminalia chebula.

<i>Gastrodia sesamoides</i> Species of orchid

Gastrodia sesamoides, commonly known as cinnamon bells or common potato orchid in Australia and as the pot-bellied orchid or cinnamon sticks in New Zealand, is a leafless, terrestrial saprophytic orchid in the family Orchidaceae. It has a thin, fleshy brown flowering stem and up to twenty five drooping, brownish, self-pollinating flowers that are white inside. Growing in a wide range of habitats, it is native to Australia and New Zealand.

Galeola faberi is an orchid species in the genus Galeola found in central and southern China, as well as in Nepal, the eastern Himalayas, Vietnam and Sumatra.

Gastrol is a phenolic compound produced by the saprophytic orchid Gastrodia elata.

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

Gastrodigenin is a phenolic compound found in the rhizome of Gastrodia elata.

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

Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.

<span class="mw-page-title-main">4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene</span> Chemical compound

4-Methyl-2,4-bis(4-hydroxyphenyl)pent-1-ene (MBP) is a metabolite of bisphenol A (BPA). MBP has potent estrogenic activity in vitro and in vivo, up to thousandfold stronger than BPA. It may also play a role in neuronal cell apoptosis and may increase risk for several forms of cancer.

<span class="mw-page-title-main">Vanilleae</span> Tribe of orchids

Vanilleae is an orchid tribe of 9 genera in the subfamily Vanilloideae.

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

Salicyl alcohol (saligenin) is an organic compound with the formula C6HOH(CH2OH. It is a white solid that is used as a precursor in organic synthesis.

References

  1. Noda, Naoki; Kobayashi, Yukio; Miyahara, Kazumoto; Fukahori, Saeko (1995). "2,4-Bis(4-hydroxybenzyl) phenol from Gastrodia elata". Phytochemistry. 39 (5): 1247–1248. doi:10.1016/0031-9422(95)00051-8. S2CID   84528243.
  2. Li, Y. M.; Zhou, Z. L.; Hong, Y. F. (1993). "Shānhú lán fēn lèi huàxué chéngfèn de yánjiū" [Studies on the phenolic derivatives from Galeola faberi Rolfe]. Yàoxué Xuébào[Acta Pharmaceutica Sinica] (in Chinese). 28 (10): 766–771. PMID   8009989. S2CID   6542806.