OJN-53009 | CAS#53-00-9 | Dehydroepiandrosterone metabolite

MedKoo Cat#: 464804 | Name: OJN-53009

Featured

Description:

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

OJN-53009 (7α-hydroxy DHEA) is an active metabolite of the endogenous steroid hormone dehydroepiandrosterone. OJN-53009 is formed from dehydroepiandrosterone via 7-hydroxylation by cytochrome P450s (CYPs). It increases antigen-induced production of anti-tetanus toxoid and anti-pertussis antigen IgGs in co-cultures of human tonsil-derived B and T cells when used at a concentration of 1 µM. OJN-53009 (6.25 mg/kg) increases serum concentrations of anti-lysozyme IgG in mice. This product has no formal name at the moment. For the convenience of communication, a temporal code name was therefore proposed according to MedKoo Chemical Nomenclature (see web page: https://www.medkoo.com/page/naming).

Chemical Structure

OJN-53009

CAS#53-00-9

Theoretical Analysis

MedKoo Cat#: 464804

Name: OJN-53009

CAS#: 53-00-9

Chemical Formula: C19H28O3

Exact Mass: 304.2038

Molecular Weight: 304.43

Elemental Analysis: C, 74.96; H, 9.27; O, 15.77

Price and Availability

Size	Price	Availability	Quantity

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

OJN-53009; OJN53009; OJN 53009; 7α-hydroxy DHEA; 7α hydroxy DHEA; 7α-hydroxy Dehydroepiandrosterone; 7α hydroxy Dehydroepiandrosterone;

IUPAC/Chemical Name

(3S,7S,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one

InChi Key

OLPSAOWBSPXZEA-JIEICEMKSA-N

InChi Code

InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1

SMILES Code

C[C@@]12[C@@]3([C@]([H])([C@]4([C@](C(CC4)=O)(C)CC3)[H])[C@H](O)C=C1C[C@@H](O)CC2)[H]

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

OJN-53009 (7α-hydroxy DHEA) is an active metabolite of the endogenous steroid hormone dehydroepiandrosterone.

In vitro activity:

TBD

In vivo activity:

This study examined in healthy male Wistar rats the in vivo antioxidant effect of dehydroepiandrosterone (DHEA) and 7alpha-hydroxy-DHEA administered by intraperitoneal injections (50 mg/kg body weight) for 2 or 7 days. DHEA and 7alpha-hydroxy-DHEA caused a decrease in body weight. DHEA treatment significantly increased liver, colon, and small intestine cell weights. After 7 days, DHEA exerted an antioxidant effect in all organs studied. Reference: Steroids. 2004 Feb;69(2):137-44. https://pubmed.ncbi.nlm.nih.gov/15013692/

Preparing Stock Solutions

The following data is based on the product molecular weight 304.43 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.

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:

Pelissier MA, Trap C, Malewiak MI, Morfin R. Antioxidant effects of dehydroepiandrosterone and 7alpha-hydroxy-dehydroepiandrosterone in the rat colon, intestine and liver. Steroids. 2004 Feb;69(2):137-44. doi: 10.1016/j.steroids.2003.12.006. PMID: 15013692.

In vitro protocol:

TBD

In vivo protocol:

1: Janšáková K, Hill M, Čelárová D, Celušáková H, Repiská G, Bičíková M, Máčová L, Ostatníková D. Alteration of the steroidogenesis in boys with autism spectrum disorders. Transl Psychiatry. 2020 Oct 6;10(1):340. doi: 10.1038/s41398-020-01017-8. PMID: 33024080; PMCID: PMC7538887. 2: Martinez-Brito D, de la Torre X, Parr MK, Botrè F. Mass spectrometric analysis of 7-oxygenated androst-5-ene structures. Influence in trimethylsilyl derivative formation. Rapid Commun Mass Spectrom. 2020 Sep 15;34(17):e8834. doi: 10.1002/rcm.8834. PMID: 32424893. 3: Offei SD, Arman HD, Baig MO, Chavez LS, Paladini CA, Yoshimoto FK. Chemical synthesis of 7-oxygenated 12α-hydroxy steroid derivatives to enable the biochemical characterization of cytochrome P450 8B1, the oxysterol 12α-hydroxylase enzyme implicated in cardiovascular health and obesity. Steroids. 2018 Dec;140:185-195. doi: 10.1016/j.steroids.2018.10.010. Epub 2018 Nov 3. PMID: 30399365; PMCID: PMC6249089. 4: Stárka L. The origin of 7alpha-hydroxy-dehydroepiandrosterone and its physiological role: a history of discoveries. Physiol Res. 2017 Sep 26;66(Suppl 3):S285-S294. doi: 10.33549/physiolres.933717. PMID: 28948812. 5: Kolatorova Sosvorova L, Sarek J, Vitku J, Kvasnica M. Synthesis of 3α-deuterated 7α-hydroxy-DHEA and 7-oxo-DHEA and application in LC-MS/MS plasma analysis. Steroids. 2016 Aug;112:88-94. doi: 10.1016/j.steroids.2016.05.001. Epub 2016 May 15. PMID: 27192427. 6: Ke Y, Gonthier R, Simard JN, Labrie F. A validated LC-MS/MS method for the sensitive quantitation of serum 7alpha hydroxy-, 7beta hydroxy- and 7keto- dehydroepiandrosterone using a novel derivatization reagent. Steroids. 2016 Apr;108:112-7. doi: 10.1016/j.steroids.2016.02.005. Epub 2016 Feb 11. PMID: 26855361. 7: Sosvorova L, Mohapl M, Hill M, Starka L, Bicikova M, Vitku J, Kanceva R, Bestak J, Hampl R. Steroid hormones and homocysteine in the outcome of patients with normal pressure hydrocephalus. Physiol Res. 2015;64(Suppl 2):S227-36. doi: 10.33549/physiolres.933072. PMID: 26680484. 8: Máčová L, Sosvorová L, Vítků J, Bičíková M, Hill M, Zamrazilová H, Sedláčková B, Stárka L. Steroid hormones related to 11beta-hydroxysteroid dehydrogenase type 1 in treated obesity. Physiol Res. 2015;64(Suppl 2):S121-33. doi: 10.33549/physiolres.933073. PMID: 26680473. 9: Sosvorova L, Vitku J, Chlupacova T, Mohapl M, Hampl R. Determination of seven selected neuro- and immunomodulatory steroids in human cerebrospinal fluid and plasma using LC-MS/MS. Steroids. 2015 Jun;98:1-8. doi: 10.1016/j.steroids.2015.01.019. Epub 2015 Feb 9. PMID: 25676787. 10: Máčová L, Bičíková M, Zamrazilová H, Hill M, Kazihnitková H, Sedláčková B, Stárka L. Reduced levels of circulating 7alpha-hydroxy-dehydroepiandrosterone in treated adolescent obese patients. Physiol Res. 2014;63(1):95-101. doi: 10.33549/physiolres.932540. Epub 2013 Nov 1. Erratum in: Physiol Res. 2014;63(3):393. PMID: 24182335. 11: Gottfried-Blackmore A, Jellinck PH, Vecchiarelli HA, Masheeb Z, Kaufmann M, McEwen BS, Bulloch K. 7α-hydroxylation of dehydroepiandrosterone does not interfere with the activation of glucocorticoids by 11β-hydroxysteroid dehydrogenase in E(t)C cerebellar neurons. J Steroid Biochem Mol Biol. 2013 Nov;138:290-7. doi: 10.1016/j.jsbmb.2013.07.001. Epub 2013 Jul 12. PMID: 23851218. 12: Sedláčková B, Dušátková L, Zamrazilová H, Matucha P, Bičíková M, Stárka L. 7-oxygenated derivatives of dehydroepiandrosterone and obesity. Prague Med Rep. 2012;113(2):147-55. doi: 10.14712/23362936.2015.29. PMID: 22691285. 13: Rijk JC, Bovee TF, Peijnenburg AA, Groot MJ, Rietjens IM, Nielen MW. Bovine liver slices: A multifunctional in vitro model to study the prohormone dehydroepiandrosterone (DHEA). Toxicol In Vitro. 2012 Sep;26(6):1014-21. doi: 10.1016/j.tiv.2012.04.012. Epub 2012 May 26. PMID: 22640920. 14: Bicikova M, Hampl R, Hill M, Ripova D, Mohr P, Putz Z. Neuro- and immunomodulatory steroids and other biochemical markers in drug-naive schizophrenia patients and the effect of treatment with atypical antipsychotics. Neuro Endocrinol Lett. 2011;32(2):141-7. PMID: 21552193. 15: Niro S, Hennebert O, Morfin R. New insights into the protective effects of DHEA1). Horm Mol Biol Clin Investig. 2010 Dec 1;4(1):489-98. doi: 10.1515/HMBCI.2010.050. PMID: 25961225. 16: Pettersson H, Lundqvist J, Norlin M. Effects of CYP7B1-mediated catalysis on estrogen receptor activation. Biochim Biophys Acta. 2010 Sep;1801(9):1090-7. doi: 10.1016/j.bbalip.2010.05.011. Epub 2010 May 26. PMID: 20553962. 17: Niro S, Hennebert O, Morfin R. A native steroid hormone derivative triggers the resolution of inflammation. Horm Mol Biol Clin Investig. 2010 Jan;1(1):11-9. doi: 10.1515/HMBCI.2010.001. PMID: 25961967. 18: Janeczko T, Dmochowska-Gładysz J, Kostrzewa-Susłow E, Białońska A, Ciunik Z. Biotransformations of steroid compounds by Chaetomium sp. KCH 6651. Steroids. 2009 Aug;74(8):657-61. doi: 10.1016/j.steroids.2009.02.006. Epub 2009 Mar 4. PMID: 19463686. 19: Le Mée S, Hennebert O, Ferrec C, Wülfert E, Morfin R. 7beta-Hydroxy- epiandrosterone-mediated regulation of the prostaglandin synthesis pathway in human peripheral blood monocytes. Steroids. 2008 Oct;73(11):1148-59. doi: 10.1016/j.steroids.2008.05.001. Epub 2008 May 14. PMID: 18555503. 20: Pettersson H, Holmberg L, Axelson M, Norlin M. CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling. FEBS J. 2008 Apr;275(8):1778-89. doi: 10.1111/j.1742-4658.2008.06336.x. Epub 2008 Mar 7. PMID: 18331353.