21-Deoxycortisone
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Hodoodo CAT#: H112028

CAS#: 1882-82-2

Description: 21-Deoxycortisone is a corticosteroid metabolite of 11-keto progesterone. It is formed from 11-keto progesterone by the cytochrome P450 (CYP) isoform CYP17A1, but can also be produced via oxidation of 21-deoxycortisol by 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2). Levels of 21-deoxycortisone are increased in patients with congenital adrenal hyperplasia, an inborn error of metabolism characterized by a deficiency in 21-hydroxylase.


Chemical Structure

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21-Deoxycortisone
CAS# 1882-82-2

Theoretical Analysis

Hodoodo Cat#: H112028
Name: 21-Deoxycortisone
CAS#: 1882-82-2
Chemical Formula: C21H28O4
Exact Mass: 344.20
Molecular Weight: 344.450
Elemental Analysis: C, 73.23; H, 8.19; O, 18.58

Price and Availability

Size Price Availability Quantity
5mg USD 250 2 Weeks
10mg USD 480 2 Weeks
25mg USD 780 2 Weeks
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Synonym: 21-Desoxycortisone; NSC-38722; 21 Desoxycortisone; NSC 38722; 21Desoxycortisone; NSC38722

IUPAC/Chemical Name: (8S,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,11(2H)-dione

InChi Key: PUKLDDOGISCFCP-JSQCKWNTSA-N

InChi Code: InChI=1S/C21H28O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-16,18,25H,4-9,11H2,1-3H3/t15-,16-,18+,19-,20-,21-/m0/s1

SMILES Code: C[C@]12[C@]([H])([C@]3([C@@]([H])([C@]4(C)C(CC3)=CC(CC4)=O)C(C2)=O)[H])CC[C@@]1(C(C)=O)O

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 2.90
DMSO 1.0 2.90

Preparing Stock Solutions

The following data is based on the product molecular weight 344.45 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Barnard L, Gent R, van Rooyen D, Swart AC. Adrenal C11-oxy C21 steroids contribute to the C11-oxy C19 steroid pool via the backdoor pathway in the biosynthesis and metabolism of 21-deoxycortisol and 21-deoxycortisone. J Steroid Biochem Mol Biol. 2017 Nov;174:86-95. doi: 10.1016/j.jsbmb.2017.07.034. Epub 2017 Jul 31. PMID: 28774496.


2: Dey R, Langer V, Roychowdhury P, Roychowdhury S, Drew MG. 21-deoxycortisone (17alpha-hydroxy-4-pregnene-3,11,20-trione). Acta Crystallogr C. 2005 Apr;61(Pt 4):o201-3. doi: 10.1107/S0108270105003756. Epub 2005 Mar 11. PMID: 15805624.


3: van Rooyen D, Yadav R, Scott EE, Swart AC. CYP17A1 exhibits 17αhydroxylase/17,20-lyase activity towards 11β-hydroxyprogesterone and 11-ketoprogesterone metabolites in the C11-oxy backdoor pathway. J Steroid Biochem Mol Biol. 2020 May;199:105614. doi: 10.1016/j.jsbmb.2020.105614. Epub 2020 Jan 30. PMID: 32007561.


4: Christakoudi S, Cowan DA, Taylor NF. Steroids excreted in urine by neonates with 21-hydroxylase deficiency. 4. Characterization, using GC-MS and GC-MS/MS, of 11oxo-pregnanes and 11oxo-pregnenes. Steroids. 2013 May;78(5):468-75. doi: 10.1016/j.steroids.2013.02.008. Epub 2013 Feb 26. PMID: 23454217.


5: Horn H, Halperin G, Weidenfeld J, Mordohovich D, Maschler I. 21-Hydroxylation of C-11-oxygenated and C-11-deoxysteroids by perfused dog adrenals. Steroids. 1977 Aug;30(2):165-7. doi: 10.1016/0039-128x(77)90078-2. PMID: 303820.


6: Koyama Y, Homma K, Miwa M, Ikeda K, Murata M, Hasegawa T. Measurement of reference intervals for urinary free adrenal steroid levels in Japanese newborn infants by using stable isotope dilution gas chromatography/mass spectrometry. Clin Chim Acta. 2013 Jan 16;415:302-5. doi: 10.1016/j.cca.2012.11.006. Epub 2012 Nov 15. PMID: 23159298.


7: Weiss M, McCance I. 21-Hydroxylation of 21-deoxycortisone by adrenal glands of a marsupial and two eutherian species. Comp Biochem Physiol B. 1974 Oct 15;49(2):227-39. doi: 10.1016/0305-0491(74)90157-6. PMID: 4425446.


8: Barnard L, du Toit T, Swart AC. Back where it belongs: 11β-hydroxyandrostenedione compels the re-assessment of C11-oxy androgens in steroidogenesis. Mol Cell Endocrinol. 2021 Apr 5;525:111189. doi: 10.1016/j.mce.2021.111189. Epub 2021 Feb 2. PMID: 33539964.


9: Saisho S, Shimozawa K, Yata J. Changes of several adrenal delta 4-steroids measured by HPLC-UV spectrometry in neonatal patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Horm Res. 1990;33(1):27-34. doi: 10.1159/000181443. PMID: 2376395.


10: Lewbart ML, Elverson RA. Determination of urinary free cortisol and cortisone by sequential thin layer and high-performance liquid chromatography. J Steroid Biochem. 1982 Aug;17(2):185-90. doi: 10.1016/0022-4731(82)90120-0. PMID: 6287108.


11: Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N. Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. doi: 10.1507/endocrj.50.783. PMID: 14709852.


12: Fenske M. Basal and HCG-stimulated testosterone production by interstitial cells of the Mongolian gerbil (Meriones unguiculatus)--II. Influence of glucocorticosteroids and steroidal precursors. Comp Biochem Physiol A Comp Physiol. 1986;85(2):273-9. doi: 10.1016/0300-9629(86)90250-1. PMID: 2876835.


13: Maschler I, Horn H. Preparation of 1,2-3H-21-deoxycortisol by incubation of 1,2-3H-17-hydroxyprogesterone with rat adrenal mitochondria. Steroids. 1976 Jan;27(1):1-3. doi: 10.1016/0039-128x(76)90064-7. PMID: 1265788.