Enterodiol

Enterodiol
Names
	Preferred IUPAC name (2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
	Other names (−)-Enterodiol
Identifiers
CAS Number	80226-00-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL471076 ;
ChemSpider	102992 ;
ECHA InfoCard	100.162.704
KEGG	C18166 ;
PubChem CID	115089;
UNII	BZF4X2AWRP ;
CompTox Dashboard (EPA)	DTXSID0047876 ;
	InChI InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1 Key: DWONJCNDULPHLV-HOTGVXAUSA-N ; InChI=1/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1 Key: DWONJCNDULPHLV-HOTGVXAUBO;
	SMILES C1=CC(=CC(=C1)O)C[C@@H](CO)[C@@H](CC2=CC(=CC=C2)O)CO;
Properties
Chemical formula	C18H22O4
Molar mass	302.370 g·mol−1
Appearance	colorless
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Enterodiol is an organic compound with the formula [HOC₆H₄CH₂CH(CH₂OH)]₂.

It is formed by the action of intestinal bacteria on lignan precursors. As such it is sometimes classified as a enterolignan or mammalian lignan.^[1]^[2] Elevated levels of enterodiol in urine are attributed consumption of tea and other lignan-rich foods.^[3]

References

^ Adlercreutz, Herman (2007). "Lignans and Human Health". Critical Reviews in Clinical Laboratory Sciences. 44 (5–6): 483–525. doi:10.1080/10408360701612942. PMID 17943494. S2CID 31753060.
^ Lampe JW (2003). "Isoflavonoid and lignan phytoestrogens as dietary biomarkers". J Nutr. 133 (Suppl 3): 956S–964S. doi:10.1093/jn/133.3.956S. PMID 12612182.
^ Adlercreutz, H.; Honjo, H.; Higashi, A.; Fotsis, T.; Hämäläinen, E.; Hasegawa, T.; Okada, H. (1991). "Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese Diet". The American Journal of Clinical Nutrition. 54 (6): 1093–1100. doi:10.1093/ajcn/54.6.1093. PMID 1659780.

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[1] Adlercreutz, Herman (2007). "Lignans and Human Health". Critical Reviews in Clinical Laboratory Sciences. 44 (5–6): 483–525. doi:10.1080/10408360701612942. PMID 17943494. S2CID 31753060.

[2] Lampe JW (2003). "Isoflavonoid and lignan phytoestrogens as dietary biomarkers". J Nutr. 133 (Suppl 3): 956S–964S. doi:10.1093/jn/133.3.956S. PMID 12612182.

[3] Adlercreutz, H.; Honjo, H.; Higashi, A.; Fotsis, T.; Hämäläinen, E.; Hasegawa, T.; Okada, H. (1991). "Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese Diet". The American Journal of Clinical Nutrition. 54 (6): 1093–1100. doi:10.1093/ajcn/54.6.1093. PMID 1659780.

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v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether