O-Desmethylangolensin - Misplaced Pages

O-Desmethylangolensin
Names

IUPAC name 1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-propanone
Identifiers
CAS Number	21255-69-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:88902
ChemSpider	80750
ECHA InfoCard	100.230.083
KEGG	C22559
PubChem CID	89472
UNII	SCY1S10OK4
CompTox Dashboard (EPA)	DTXSID40873154
InChI InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3Key: JDJPNKPFDDUBFV-UHFFFAOYSA-N
SMILES CC(c1ccc(cc1)O)C(=O)c2ccc(cc2O)O
Properties
Chemical formula	C₁₅H₁₄O₄
Molar mass	258.273 g·mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318, H410
Precautionary statements	P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

O-Desmethylangolensin (O-DMA) is a phytoestrogen. It is an intestinal bacterial metabolite of the soy phytoestrogen daidzein. It produced in some people, deemed O-DMA producers, but not others. O-DMA producers were associated with 69% greater mammographic density and 6% bone density.

References

^ Frankenfeld, C. L. (2011). "O-Desmethylangolensin: The Importance of Equol's Lesser Known Cousin to Human Health". Advances in Nutrition. 2 (4): 317–324. doi:10.3945/an.111.000539. PMC 3125681. PMID 22332073.

Xenoestrogens

Phytoestrogens

Flavanones	Hesperetin Liquiritigenin Naringenin Pinocembrin
Flavones	Acacetin 7,8-Dihydroxyflavone Mirificin
Prenylflavonoids	8-Prenylnaringenin 6-Prenylnaringenin 8-Geranylnaringenin 6,8-Diprenylnaringenin Icaritin
Isoflavones	Biochanin A Daidzein Daidzin Formononetin Genistein Genistin Glycitein Ononin Prunetin Puerarin Tectorigenin
Isoflavanes	Equol (S-Equol) Glabridin
Dihydrochalcones	Phloretin Phlorizin
Isoflavenes	Glabrene
Coumestans	Coumestan Coumestrol Desmethylwedelolactone Wedelolactone
Lignans	Enterodiol Enterolactone
Flavonolignans	Silybin Cinchonain-Ib
Flavonols	Quercetin
Others	Deoxymiroestrol Miroestrol Resveratrol α-Isosparteine

Mycoestrogens

Derivatives	D-Penicillamine

Synthetic

Metalloestrogens

Aluminium
Antimony
Arsenite
Barium
Cadmium
Chromium
Cobalt
Copper
Lead
Mercury
Nickel
Selenite
Tin
Vanadate

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

v t e Isoflavanes
Isoflavanes:	Equol Glabridin Laxiflorane Lonchocarpane

Soy (Glycine max)

General

Soy-based
dishes

Plant milk

Meat analogues

Sauces and
condiments

Soy sauce based	Ganjang Ponzu Sweet soy sauce Tamari Teriyaki Tsuyu Yìn yóu
Pastes	Doenjang Doubanjiang Miso Sweet bean sauce Yellow soybean paste Tương
Fermented bean	Akhuni Fermented bean curd Douchi Kinema Tauco Nattō

Other foods

Biochemicals

Phytoestrogens	Genistein Genistin Glycitein Glycitin Ononin Daidzein Equol (metabolite) O-DMA (metabolite) Daidzin (leaves)
Globulins (proteins)	Beta-conglycinin Glycinin
PHAs (lectins)	Soybean agglutinin (lectin)
Enzymes	Beta-amylase Lipoxygenase Cysteine proteases
Trypsin inhibitors	Kunitz inhibitor Bowman-Birk inhibitor
Other	Soy lecithin (mix of Phospholipids) Lunasin Unsaponifiables Tocopherols Sterols Antinutrients Phytates Protease Inhibitors Cystatins

Companies

Other

Diet for a Small Planet
Kikkoman Soy Sauce Museum
William Shurtleff and Akiko Aoyagi
Yuasa, artisan town of historic soy sauce distilleries

Category: Soybeans

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See also

References