A metabolite of cortisol and 11-keto testosterone
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Parent Compound(s)
20739Hydrocortisone
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11-oxo Etiocholanolone

Item No. 35009

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-3α-hydroxy-androstane-11,17-dione
CAS Number
739-27-5
Synonyms
  • 5β-Androstane-3α-ol-11,17-dione
  • 11-keto Etiocholanolone
  • NSC 53896
Molecular Formula
C19H28O3
Formula Weight
304.4
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble
SMILES
C[C@@]12[C@]3([H])[C@](CC[C@]1([H])C[C@@H](CC2)O)([H])[C@@]4([H])[C@](CC3=O)(C(CC4)=O)C
InChi Code
InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-14,17,20H,3-10H2,1-2H3/t11-,12-,13+,14+,17-,18+,19+/m1/s1
InChi Key
IUNYGQONJQTULL-UKZLPJRTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    11-oxo Etiocholanolone is a metabolite of cortisol (hydrocortisone; Item No. 20739) and 11-keto testosterone.1,2 It is formed from cortisol via cortisone (Item No. 30763) and tetrahydrocortistone (Item No. 34344) intermediates, and it is formed from 11-keto testosterone via 5β-11-keto dihydrotestosterone and 3α-11-keto etiocholanediol intermediates. Urinary levels of 11-oxo etiocholanolone increase during pregnancy and are elevated in patients with uterine leiomyomas.3,4 Fecal levels of 11-oxo etiocholanolone have been used as a marker of stress in domestic livestock and free-range ruminants.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schiffer, L., Barnard, L., Baranowski, E.S., et al. Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: A comprehensive review. J. Steroid Biochem. Mol. Biol. 194, 105439 (2019).

    2. Barnard, L., Nikolaou, N., Louw, C., et al. The A-ring reduction of 11-ketotestosterone is efficiently catalysed by AKR1D1 and SRD5A2 but not SRD5A1. J. Steroid Biochem. Mol. Biol. 202, 105724 (2020).

    3. Birke, G., Gemzell, C.A., Plantin, L.O., et al. Plasma levels of 17-hydroxycorticosteroids and urinary excretion pattern of keto-steroids in normal pregnancy. Acta Endocrinol. (Copenh.) 27(4), 389-402 (1958).

    4. Jung, B.H., Bai, S.W., and Chung, B.C. Endogenous urinary steroids in premenopausal women with uterine leiomyomas. Int. J. Gynaecol. Obstet. 84(1), 55-60 (2004).

    5. Molina-García, L., Pérez, J.M., Sarasa, M., et al. HPLC-QTOF method for quantifying 11-ketoetiocholanolone, a cortisol metabolite, in ruminants' feces: Optimization and validation. Ecol. Evol. 8(18), 9218-9228 (2018).