2-Hydroxyestriol

2-Hydroxyestriol, also known as estra-1,3,5(10)-triene-2,3,16α,17β-tetrol, is an endogenous catechol estrogen and metabolite of estriol. It is a suspected carcinogen of carcinogenicity category 2.[1]

Selected biological properties of endogenous estrogens in rats

Estrogen	ER RBA (%)	Uterine weight (%)	Uterotrophy	LH levels (%)	SHBG RBA (%)
Control	–	100	–	100	–
Estradiol	100	506 ± 20	+++	12–19	100
Estrone	11 ± 8	490 ± 22	+++	?	20
Estriol	10 ± 4	468 ± 30	+++	8–18	3
Estetrol	0.5 ± 0.2	?	Inactive	?	1
17α-Estradiol	4.2 ± 0.8	?	?	?	?
2-Hydroxyestradiol	24 ± 7	285 ± 8	+^b	31–61	28
2-Methoxyestradiol	0.05 ± 0.04	101	Inactive	?	130
4-Hydroxyestradiol	45 ± 12	?	?	?	?
4-Methoxyestradiol	1.3 ± 0.2	260	++	?	9
4-Fluoroestradiol^a	180 ± 43	?	+++	?	?
2-Hydroxyestrone	1.9 ± 0.8	130 ± 9	Inactive	110–142	8
2-Methoxyestrone	0.01 ± 0.00	103 ± 7	Inactive	95–100	120
4-Hydroxyestrone	11 ± 4	351	++	21–50	35
4-Methoxyestrone	0.13 ± 0.04	338	++	65–92	12
16α-Hydroxyestrone	2.8 ± 1.0	552 ± 42	+++	7–24	<0.5
2-Hydroxyestriol	0.9 ± 0.3	302	+^b	?	?
2-Methoxyestriol	0.01 ± 0.00	?	Inactive	?	4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: ^a = Synthetic (i.e., not endogenous). ^b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

2-Hydroxyestriol

Names
IUPAC name (8R,9S,13S,14S,16R,17R)-13-Methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,3,16,17-tetrol[1]
Other names Estra-1,3,5(10)-triene-2,3,16α,17β-tetrol
Identifiers
CAS Number	1232-80-0^Y
3D model (JSmol)	Interactive image
ChemSpider	8510654
PubChem CID	10335195
UNII	XS3NDJ547R^Y
InChI InChI=1S/C18H24O4/c1-18-5-4-10-11(13(18)8-16(21)17(18)22)3-2-9-6-14(19)15(20)7-12(9)10/h6-7,10-11,13,16-17,19-22H,2-5,8H2,1H3/t10-,11+,13-,16+,17-,18-/m0/s1 Key: ZUGCDOZAVASBQT-SLVREZFOSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=CC(=C(C=C34)O)O
Properties
Chemical formula	C18H24O4
Molar mass	304.386 g·mol^−1
Hazards
GHS hazard statements	H351
GHS precautionary statements	P201, P202, P281, P308+313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• 4-Hydroxyestriol
• 2-Methoxyestriol

References

1. "2-HYDROXYESTRIOL". National Center for Biotechnology Information. 17 December 2016. Archived from the original on 26 December 2016. Retrieved 26 December 2016.