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SMB01343

Sigma-Aldrich

Tetrahydrocortisol

≥95% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C21H34O5
Numéro CAS:
53-02-1
Poids moléculaire :
366.49
Numéro MDL:
MFCD00067597
Code UNSPSC :
51420000
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Pureté

≥95% (HPLC)

Forme

solid

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

AODPIQQILQLWGS-GXBDJPPSSA-N

Description générale

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.

Caractéristiques et avantages

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

Autres remarques

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Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
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
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
Susanna Bianzano et al.
Clinical diabetes and endocrinology, 7(1), 16-16 (2021-08-16)
The study characterizes safety, tolerability, pharmacokinetic and pharmacodynamic profiles of single rising doses of the 11beta-hydroxysteroid dehydrogenase-1 (11beta-HSD1) inhibitor BI 187004 in healthy men with overweight or obesity. This was a randomized, double-blind, parallel group, placebo-controlled study with administration of

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