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SMB01343

Sigma-Aldrich

Tetrahydrocortisol

≥95% (HPLC)

Synonym(s):

5β-Tetrahydrocortisol, THF, Tetrahydro F, Tetrahydrocompound F, Tetrahydrohydrocortisone, Urocortisol

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About This Item

Empirical Formula (Hill Notation):
C21H34O5
CAS Number:
53-02-1
Molecular Weight:
366.49
MDL number:
MFCD00067597
UNSPSC Code:
51420000

Quality Level

200

assay

≥95% (HPLC)

form

solid

storage temp.

2-8°C

SMILES string

O=C(CO)[C@@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])[C@@H](O)C[C@@]21C

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

Related Categories

General description

Tetrahydrocortisol, also known as Urocortisol, falls under the corticosteroid category. It serves as a byproduct of cortisol, playing a potential role in the complex transformation of cortisol into cortoic acids. This substance is naturally generated by lymphocytes and tends to be more prevalent in patients with cancer, adding to its significance in metabolomics research. Additionally, Tetrahydrocortisol is an endogenous derivative of hydrocortisone and acts as an intermediary in the synthesis of β-cortol. Its formation involves a conversion process from cortisol, triggered by the enzyme steroid 5β-reductase and subsequent dehydrogenation carried out by 20β-hydroxysteroid dehydrogenase (20β-HSD) within the liver. Notably, the levels of 5β-tetrahydrocortisol found in urine have been employed as an indicator of cortisol production and are linked with metabolic syndrome, particularly in individuals with obesity. Furthermore, Tetrahydrocortisol and Tetrahydrocortisone are steroids and inactive metabolites of hydrocortisone or cortisol. The THF/THE ratio is a valuable tool for evaluating patient health and diagnosing various medical conditions, highlighting Tetrahydrocortisol′s significance in the fields of biochemical research and metabolomics.

Application

Tetrahydrocortisol finds application in biochemical and metabolomics research.

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Judith E Heida et al.
American journal of nephrology, 51(11), 861-870 (2020-11-05)
Patients with autosomal dominant polycystic kidney disease (ADPKD) are treated with a vasopressin V2 receptor antagonist (V2RA) to slow disease progression. This drug increases vasopressin considerably in these patients with already elevated baseline levels. Vasopressin is known to stimulate the
Joëlle C Schutten et al.
Clinical endocrinology, 94(2), 150-157 (2020-10-09)
Increasing magnesium intake might reduce the risk of cardiovascular disease (CVD). Whether potential effects on cortisol contribute to these beneficial effects on cardiovascular health remains unclear. We therefore studied effects of long-term oral magnesium supplementation on glucocorticoid metabolism, specifically on
Domenica De Santis et al.
Frontiers in endocrinology, 12, 681974-681974 (2021-09-10)
Apparent mineralocorticoid excess (AME) is an autosomal recessive disorder caused by the 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2) enzyme deficiency, traditionally assessed by measuring either the urinary cortisol metabolites ratio (tetrahydrocortisol+allotetrahydrocortisol/tetrahydrocortisone, THF+5αTHF/THE) or the urinary cortisol/cortisone (F/E) ratio. Exosomal mRNA is

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