An endogenous metabolite of cortisol
Related Products
Metabolite(s)
36224β-Cortolone
Parent Compound(s)
20739Hydrocortisone
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5β-Tetrahydrocortisol

Item No. 34195

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β,11β)-3,11,17,21-tetrahydroxy-pregnan-20-one
CAS Number
53-02-1
Synonyms
  • NSC 57431
Molecular Formula
C21H34O5
Formula Weight
366.5
Purity
≥98%
Formulation (Request formulation change)
A solid
SMILES
C[C@@]12[C@](CC[C@]2(O)C(CO)=O)([H])[C@@]3([H])[C@@]([C@H](C1)O)([H])[C@@]4([C@](C[C@@H](CC4)O)([H])CC3)C
InChi Code
InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1
InChi Key
AODPIQQILQLWGS-GXBDJPPSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $110

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    10 mg

    $209

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    25 mg

    $440

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    Product Description

    5β-Tetrahydrocortisol is an endogenous metabolite of hydrocortisone (cortisol; Item No. 20739).1,2 It is also an intermediate in the biosynthesis of β-cortol (Item No. 33412).2 It is formed from cortisol by steroid 5β-reductase and is dehydrogenated by 20β-hydroxysteroid dehydrogenase (20β-HSD) to produce β-cortol in the liver.3,1,2 Urinary levels of 5β-tetrahydrocortisol have been used as a marker for cortisol production and are associated with metabolic syndrome in obese individuals.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shackleton, C.H.L. Role of a disordered steroid metabolome in the elucidation of sterol and steroid biosynthesis. Lipids 47(1), 1-12 (2012).

    2. 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).

    3. Kosicka, K., Siemiątkowska, A., Pałka, D., et al. Detailed analysis of cortisol, cortisone and their tetrahydro- and allo-tetrahydrometabolites in human urine by LC-MS/MS. J. Pharm. Biomed. Anal. 140, 174-181 (2017).

    4. Baudrand, R., Campino, C., Carvajal, C.A., et al. Increased urinary glucocorticoid metabolites are associated with metabolic syndrome, hypoadiponectinemia, insulin resistance and β cell dysfunction. Steroids 76(14), 1575-1581 (2011).