Enterodiol: Difference between revisions

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			{{short description\|Lignan formed by the action of intestinal bacteria on lignan precursors found in plants.}}
	{{chembox
			{{Chembox
⚫	\| verifiedrevid = ~~405873208~~
			\| Verifiedfields = changed
	\|ImageFile=Enterodiol.png
			\| Watchedfields = changed
⚫	\|ImageSize=180px
		⚫	\| verifiedrevid = 443726976
⚫	\|~~IUPACName~~= (2''R'',3''R'')-2,3-~~bis~~butane-1,4-diol
	\|~~OtherNames~~=~~(-)-~~Enterodiol		\| ImageFile = Enterodiol.png
		⚫	\| ImageSize = 180px
		⚫	\| PIN = (2''R'',3''R'')-2,3-Bisbutane-1,4-diol
			\| OtherNames = (−)-Enterodiol
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| CASNo=80226-00-2		\| CASNo = 80226-00-2
	\| PubChem=115089
	\| ~~UNII~~ = ~~BZF4X2AWRP~~		\| PubChem = 115089
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| SMILES=C1=CC(=CC(=C1)O)C(CO)(CC2=CC(=CC=C2)O)CO
			\| UNII = BZF4X2AWRP
⚫	}}
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = C18166
		⚫	\| SMILES = C1=CC(=CC(=C1)O)C(CO)(CC2=CC(=CC=C2)O)CO
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 102992
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 471076
			\| 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
			\| InChIKey = DWONJCNDULPHLV-HOTGVXAUBO
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 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
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = DWONJCNDULPHLV-HOTGVXAUSA-N
		⚫	}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| C=18\|H=22\|O=4		\| C=18\|H=22\|O=4
	\| Appearance=		\| Appearance = colorless
	\| Density=		\| Density =
	\| MeltingPt=		\| MeltingPt =
	\| BoilingPt=		\| BoilingPt =
	\| Solubility=		\| Solubility =
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards =
	\| FlashPt=		\| FlashPt =
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}

			'''Enterodiol''' is an organic compound with the formula <sub>2</sub>.
	'''Enterodiol''' is a ] formed by the action of intestinal bacteria on lignan precursors found in plants.<ref>{{cite journal \| author = Lampe JW \| title = Isoflavonoid and lignan phytoestrogens as dietary biomarkers \| journal = J Nutr \| year = 2003 \| volume = 133 \| issue = Suppl 3 \| pages = 956S–964S \| pmid = 12612182}}</ref>

			It is formed by the action of intestinal bacteria on ] precursors. As such it is sometimes classified as a ] or mammalian lignan.<ref>{{cite journal \|doi=10.1080/10408360701612942\|title=Lignans and Human Health\|year=2007\|last1=Adlercreutz\|first1=Herman\|journal=Critical Reviews in Clinical Laboratory Sciences\|volume=44\|issue=5–6\|pages=483–525\|pmid=17943494\|s2cid=31753060}}</ref><ref>{{cite journal \| author = Lampe JW \| title = Isoflavonoid and lignan phytoestrogens as dietary biomarkers \| journal = J Nutr \| year = 2003 \| volume = 133 \| issue = Suppl 3 \| pages = 956S–964S \| pmid = 12612182 \| doi=10.1093/jn/133.3.956S\| doi-access = free }}</ref> Elevated levels of enterodiol in urine are attributed consumption of tea and other lignan-rich foods.<ref>{{cite journal \|doi=10.1093/ajcn/54.6.1093\|title=Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese Diet\|year=1991\|last1=Adlercreutz\|first1=H.\|last2= Honjo\|first2=H.\|last3=Higashi\|first3=A.\|last4=Fotsis\|first4=T.\|last5= Hämäläinen\|first5=E.\|last6=Hasegawa\|first6=T.\|last7=Okada\|first7=H.\|journal=The American Journal of Clinical Nutrition\|volume=54\|issue=6\|pages=1093–1100\|pmid=1659780\|doi-access=free}}</ref>

	==References==		==References==
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	]		]
	]		]
			]

	{{~~natural-phenol~~-stub}}		{{aromatic-stub}}

Latest revision as of 16:02, 21 October 2024

Lignan formed by the action of intestinal bacteria on lignan precursors found in plants.

Enterodiol
Names

Preferred IUPAC name (2R,3R)-2,3-Bisbutane-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/s1Key: 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/s1Key: DWONJCNDULPHLV-HOTGVXAUBO
SMILES C1=CC(=CC(=C1)O)C(CO)(CC2=CC(=CC=C2)O)CO
Properties
Chemical formula	C₁₈H₂₂O₄
Molar mass	302.370 g·mol
Appearance	colorless
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Enterodiol is an organic compound with the formula 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. Elevated levels of enterodiol in urine are attributed consumption of tea and other lignan-rich foods.

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.

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

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