MedKoo Cat#: 584115 | Name: Tetrahydrocortisol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tetrahydrocortisol, also known as Urocortisol, is a steroid that is a metabolite of cortisone and has a possible role as an intermediate in the biotransformation of cortisol to cortoic acids.

Chemical Structure

Tetrahydrocortisol
CAS#53-02-1

Theoretical Analysis

MedKoo Cat#: 584115

Name: Tetrahydrocortisol

CAS#: 53-02-1

Chemical Formula: C21H34O5

Exact Mass: 366.2406

Molecular Weight: 366.49

Elemental Analysis: C, 68.82; H, 9.35; O, 21.83

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Tetrahydrocortisol; Urocortisol; Ba 2682; Ba-2682; Ba2682; NSC 57431; NSC-57431; NSC57431
IUPAC/Chemical Name
3alpha,11beta,17,21-Tetrahydroxy-5beta-pregnan-20-one
InChi Key
AODPIQQILQLWGS-GXBDJPPSSA-N
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
SMILES Code
C[C@@]12[C@](C(CO)=O)(O)CC[C@@]1([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])[C@@H](O)C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 366.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zumoff B, Monder C, Bradlow HL. Studies in the biotransformation of cortisol to the cortoic acids in man. II. The central role of tetrahydrocortisol and tetrahydrocortisone as intermediates. J Clin Endocrinol Metab. 1977 Apr;44(4):647-50. PubMed PMID: 849978. 2: Meklat N, Tabet JC, de Ceaurriz J. Urine ratio of tetrahydrocortisol to tetrahydrodeoxycortisol to screen for the systemic administration of cortisone and hydrocortisone. Forensic Sci Int. 2009 Mar 10;185(1-3):e13-7. doi: 10.1016/j.forsciint.2008.12.011. Epub 2009 Jan 29. PubMed PMID: 19185436. 3: Panin LE, Kunitsyn VG, Poliakov LM. [Mechanisms of interaction of tetrahydrocortisol and its complex with apolipoprotein A-I and DNA regulatory cis-elements of CC(GCC)5/GG(CGG)5 type]. Biofizika. 2008 Jan-Feb;53(1):42-7. Russian. PubMed PMID: 18488499. 4: Panin LE, Knyazev RA, Sumenkova DV, Polyakov LM. Effect of complexes of apolipoprotein A-I with tetrahydrocortisol and pregnenolone on protein biosynthesis in rat hepatocytes culture. Bull Exp Biol Med. 2007 Sep;144(3):291-3. PubMed PMID: 18457017. 5: Yamashita K, Nakagawa R, Okuyama M, Honma S, Takahashi M, Numazawa M. Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. Steroids. 2008 Aug;73(7):727-37. doi: 10.1016/j.steroids.2008.02.009. Epub 2008 Feb 26. PubMed PMID: 18394666. 6: Panin LE, Tuzikov FV, Tuzikova NA, Pliakov LM. [Features of interaction of complexes cortisol-apolipoprotein A-I and tetrahydrocortisol-apolipoprotein A-I with eukariotic DNA]. Mol Biol (Mosk). 2006 Mar-Apr;40(2):300-9. Russian. PubMed PMID: 16637271. 7: Turpeinen U, Markkanen H, Sane T, Hämäläinen E. Determination of free tetrahydrocortisol and tetrahydrocortisone ratio in urine by liquid chromatography-tandem mass spectrometry. Scand J Clin Lab Invest. 2006;66(2):147-59. PubMed PMID: 16537248. 8: Raffaelli A, Saba A, Vignali E, Marcocci C, Salvadori P. Direct determination of the ratio of tetrahydrocortisol+allo-tetrahydrocortisol to tetrahydrocortisone in urine by LC-MS-MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 18;830(2):278-85. Epub 2005 Nov 23. PubMed PMID: 16310418. 9: Panin LE, Tuzikov FV, Gimautdinova OI. Tetrahydrocortisol-apolipoprotein A-I complex specifically interacts with eukaryotic DNA and GCC elements of genes. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):309-18. PubMed PMID: 14698212. 10: Stiefel P, García-Morillo JS, Jimenez L, Pamies E, Miranda ML, Carneado J, Villar J, Leal-Cerro A. Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome. Endocrine. 2002 Aug;18(3):279-84. PubMed PMID: 12450320. 11: Panin LE, Gimautdinova OI, Kuznetsov PA, Akimzhanova MV, Tuzikov FV. Effect of tetrahydrocortisol-apolipoprotein A-I complex on the secondary structure of eukaryotic DNA and its interaction with RNA-polymerase. Biochemistry (Mosc). 2002 Jul;67(7):790-4. PubMed PMID: 12139478. 12: Panin LE, Tuzikov FV, Tuzikova NA, Gimautdinova OI, Poliakov LM. [Interaction of tetrahydrocortisol-apolipoprotein A-I complex with eukaryotic DNA and with single-stranded oligonucleotides]. Mol Biol (Mosk). 2002 Jan-Feb;36(1):96-102. Russian. PubMed PMID: 11862720. 13: Panin LE, Tuzikov FV, Tuzikova NA, Usynin IF, Gimautdinova OI. [Effect of tetrahydrocortisol-apolipoprotein A-I complex on RNA polymerase interaction with eukaryotic DNA and the rate of protein biosynthesis in hepatocytes]. Bioorg Khim. 2001 Mar-Apr;27(2):114-9. Russian. PubMed PMID: 11357395. 14: Furuta T, Namekawa T, Shibasaki H, Kasuya Y. Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans. Steroids. 1999 Dec;64(12):805-11. PubMed PMID: 10576214. 15: Furuta T, Namekawa T, Shibasaki H, Kasuya Y. Simultaneous determination of tetrahydrocortisol and tetrahydrocortisone in human plasma and urine by stable isotope dilution mass spectrometry. J Chromatogr B Biomed Sci Appl. 1998 Mar 20;706(2):181-90. PubMed PMID: 9551804. 16: Clark AF, Lane D, Wilson K, Miggans ST, McCartney MD. Inhibition of dexamethasone-induced cytoskeletal changes in cultured human trabecular meshwork cells by tetrahydrocortisol. Invest Ophthalmol Vis Sci. 1996 Apr;37(5):805-13. PubMed PMID: 8603865. 17: Southren AL, Wandel T, Gordon GG, Weinstein BI. Treatment of glaucoma with 3 alpha, 5 beta-tetrahydrocortisol: a new therapeutic modality. J Ocul Pharmacol. 1994 Spring;10(1):385-91. PubMed PMID: 8207341. 18: Teicher BA, Sotomayor EA, Huang ZD, Ara G, Holden S, Khandekar V, Chen YN. beta-cyclodextrin tetradecasulfate/tetrahydrocortisol +/- minocycline as modulators of cancer therapies in vitro and in vivo against primary and metastatic Lewis lung carcinoma. Cancer Chemother Pharmacol. 1993;33(3):229-38. PubMed PMID: 8269604. 19: Southren AL, l'Hommedieu D, Gordon GG, Weinstein BI. Intraocular hypotensive effect of a topically applied cortisol metabolite: 3 alpha, 5 beta-tetrahydrocortisol. Invest Ophthalmol Vis Sci. 1987 May;28(5):901-3. PubMed PMID: 3570698. 20: Aranoff G, Rösler A. Urinary tetrahydrocortisone and tetrahydrocortisol glucosiduronates in normal newborns, children and adults. Acta Endocrinol (Copenh). 1980 Jul;94(3):371-5. PubMed PMID: 7424479.