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K1001

Sigma-Aldrich

β-Estradiol-6-one

Synonym(s):

1,3,5-Estratriene-3,17β-diol-6-one, 3,17β-Dihydroxy-1,3,5(10)-estratrien-6-one, 6-Ketoestradiol

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About This Item

Empirical Formula (Hill Notation):
C18H22O3
CAS Number:
571-92-6
Molecular Weight:
286.37
Beilstein:
3208779
MDL number:
MFCD00056457
UNSPSC Code:
12352200
PubChem Substance ID:
329817122
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98.00% (TLC)

form

powder

solubility

chloroform: methanol (1:1): 19.60-20.40 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3[C@@H](CC(=O)c4cc(O)ccc34)[C@@H]1CC[C@@H]2O

InChI

1S/C18H22O3/c1-18-7-6-12-11-3-2-10(19)8-14(11)16(20)9-13(12)15(18)4-5-17(18)21/h2-3,8,12-13,15,17,19,21H,4-7,9H2,1H3/t12-,13-,15+,17+,18+/m1/s1

InChI key

ZHTDDOWJIRXOMA-YVEZLPLXSA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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H Mikola et al.
Bioconjugate chemistry, 3(2), 182-186 (1992-03-01)
(Aminooxy)butyl- and -hexylamines and alcohols were synthesized by the Ing-Manske modification of the Gabriel synthesis. The aminooxy group of these heterobifunctional spacer reagents is a far more powerful nucleophile than the amino or hydroxy group because of the oxygen atom
Anna Bogucka-Kocka et al.
Journal of AOAC International, 94(1), 9-16 (2011-03-12)
Eighteen species belonging to the Carex genus were checked for the presence and the amount of eight phenolic acids (p-hydroxybenzoic, vanillic, caffeic, syringic, protocatechuic, p-coumaric, sinapic, and ferulic) by means of HPLC. Both the free and bonded phenolic acids were
M Adamczyk et al.
Steroids, 64(4), 283-290 (1999-07-10)
The 5 and 6-isomers of O-(fluoresceinylmethyl)hydroxylamine reacted with a representative sample of oxo-steroids (6-oxoestradiol, estrone, norethindrone, cortisol, progesterone, and digitoxin-dialdehyde) to produce O-(fluoresceinylmethyl)oxime conjugates in a single step in 24-84% yield after preparative high performance liquid chromotography.
M Adamczyk et al.
Steroids, 62(6), 462-467 (1997-06-01)
6-Oxoestradiol (2) was protected as its bis[(2-trimethylsilylethoxy)methyl] ether (4) and converted to the corresponding oxime (4). The oxime (4) on reduction with zinc in ethanol afforded the bis-SEM ether of 6-alpha-aminoestradiol (5) in 96% epimeric excess. Subsequently, 5 was hydrolyzed
M Numazawa et al.
Biochemical pharmacology, 47(4), 717-726 (1994-02-11)
Aromatase catalyzes the conversion of androst-4-ene-3,17-dione to estrogen through sequential oxygenations at the 19-methyl group. Androst-4-ene-3,6,17-trione (AT) is a suicide substrate of aromatase, and the mechanism of inactivation of aromatase has been postulated to involve enzymatic oxygenation at the 19-position.
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