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MedKoo Cat#: 414043 | Name: Epiestriol
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Description:

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

Epiestriol is a minor and weak endogenous estrogen, and the 16β-epimer of estriol. Epiestriol is used clinically in the treatment of acne.

Chemical Structure

Epiestriol
Epiestriol
CAS#547-81-9

Theoretical Analysis

MedKoo Cat#: 414043

Name: Epiestriol

CAS#: 547-81-9

Chemical Formula: C18H24O3

Exact Mass: 288.1725

Molecular Weight: 288.39

Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Epiestriol; Epiestriolum; Epiestriolo; Epioestriol; 16-Epiestriol; 16-Epiestratriol; 16-epi-Estriol; 16-EpiE3; 16β-hydroxy-17α-Estradiol; NSC 26646; NSC26646; NSC-26646;
IUPAC/Chemical Name
(8R,9S,13S,14S,16S,17R)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol
InChi Key
PROQIPRRNZUXQM-ZMSHIADSSA-N
InChi Code
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1
SMILES Code
OC1=CC=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)[C@@H](O)C[C@@]4([H])[C@]3([H])CCC2=C1
Appearance
Solid powder
Purity
>90% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 288.39 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: Skariyachan S, Muddebihalkar AG, Badrinath V, Umashankar B, Eram D, Uttarkar A, Niranjan V. Natural epiestriol-16 act as potential lead molecule against prospective molecular targets of multidrug resistant Acinetobacter baumannii- Insight from in silico modelling and in vitro investigations. Infect Genet Evol. 2020 Aug;82:104314. doi: 10.1016/j.meegid.2020.104314. Epub 2020 Apr 5. PMID: 32268193. 2: Ali ES, Mangold C, Peiris AN. Estriol: emerging clinical benefits. Menopause. 2017 Sep;24(9):1081-1085. doi: 10.1097/GME.0000000000000855. PMID: 28375935. 3: Miller E, Bates R, Bjorndahl J, Allen D, Burgio D, Bouma C, Stoll J, Latman N. 16-Epiestriol, a novel anti-inflammatory nonglycogenic steroid, does not inhibit IFN-gamma production by murine splenocytes. J Interferon Cytokine Res. 1998 Nov;18(11):921-5. doi: 10.1089/jir.1998.18.921. PMID: 9858313. 4: Mukherjee TK, Nathan L, Dinh H, Reddy ST, Chaudhuri G. 17-epiestriol, an estrogen metabolite, is more potent than estradiol in inhibiting vascular cell adhesion molecule 1 (VCAM-1) mRNA expression. J Biol Chem. 2003 Apr 4;278(14):11746-52. doi: 10.1074/jbc.M207800200. Epub 2003 Jan 23. PMID: 12547825. 5: Latman NS, Kishore V, Bruot BC. 16-epiestriol: an anti-inflammatory steroid without glycogenic activity. J Pharm Sci. 1994 Jun;83(6):874-7. doi: 10.1002/jps.2600830623. PMID: 9120824. 6: Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M. Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol. Drug Metab Dispos. 2013 Mar;41(3):582-91. doi: 10.1124/dmd.112.049072. Epub 2013 Jan 3. PMID: 23288867. 7: Fribourg S. Estriol. JAMA. 1978 Sep 1;240(9):830. PMID: 353316. 8: Trisequens. Drug Ther Bull. 1981 Jul 31;19(16):63-4. PMID: 7274066. 9: Sharoukhova KS, Murav'eva NI. Biosintez éstriola [Biosynthesis of estriol]. Vopr Med Khim. 1966 Nov-Dec;12(6):563-8. Russian. PMID: 4877572. 10: Lim JL, Zheng L, Berridge MS, Tewson TJ. The use of 3-methoxymethyl-16 beta, 17 beta-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16 alpha-fluoroestradiol. Nucl Med Biol. 1996 Oct;23(7):911-5. doi: 10.1016/s0969-8051(96)00126-6. PMID: 8971859. 11: Peters G. Ostriol [Estriol]. Med Klin. 1968 Nov 22;63(47):1877-8. German. PMID: 4886193. 12: Battaglia GB, Morresi G, Camptaelli C, Messeri G. Valore clinico dell'estriolo plasmatico parte prima: suo rapporto con l'estriolo urinario nelle garvidanze noramli [Clinicacy]. Ann Ostet Ginecol Med Perinat. 1976 May- Jun;97(3):136-55. Italian. PMID: 1015748. 13: KATZMAN PA, MONTELEONE JA, RHONE JR, NOFFSINGER J, REICH H, HUFFMAN MN. 16-Epiestriol-3-allyl ether, an ovarian stimulator (estra-1, 3, 5(10)-trien, 3-allyloxy, 16beta,17beta-diol). Acta Physiol Pharmacol Neerl. 1962;10:335-42. PMID: 14454422. 14: STRAUSS JS, POCHI PE. Sebum production during 16-epiestriol administration. Arch Dermatol. 1962 Dec;86:757-60. doi: 10.1001/archderm.1962.01590120055009. PMID: 13978807. 15: Abraham S. Recovery after childbirth. Med J Aust. 1990 Apr 2;152(7):387. doi: 10.5694/j.1326-5377.1990.tb125240.x. PMID: 2093822. 16: MATSUMOTO K, SEKI T. CHROMATOGRAPHIC SEPARATION OF ESTRIOL, 16-KETOESTRADIOL-17BETA, 16-EPIESTRIOL, ESTRADIOL-17ALPHA, ESTRADIOL-17BETA, ESTRONE AND 2-METHOXYESTRONE ON THE COLUMN OF PARTIALLY ESTERIFIED CARBOXYLIC ACID TYPE ION EXCHANGE RESIN. Endocrinol Jpn. 1963 Jun;10:136-41. doi: 10.1507/endocrj1954.10.136. PMID: 14050082. 17: MATSUMOTO K, SEKI T. A CHEMICAL METHOD FOR THE QUANTITATIVE DETERMINATION OF ESTRIOL, 16-EPIESTRIOL, ESTRADIOL-17 BETA AND ESTRONE IN HUMAN MALE AND NON- PREGNANCY URINE. Endocrinol Jpn. 1963 Sep;10:183-9. doi: 10.1507/endocrj1954.10.183. PMID: 14066293. 18: Englund DE, Elamsson KB, Johansson ED. Bioavailability of oestriol. Acta Endocrinol (Copenh). 1982 Jan;99(1):136-40. doi: 10.1530/acta.0.0990136. PMID: 7058673. 19: Tanaka K. [Glutamate transporter dysfunction and major mental illnesses]. Nihon Rinsho. 2016 Jan;74(1):163-73. Japanese. PMID: 26793898. 20: Head KA. Estriol: safety and efficacy. Altern Med Rev. 1998 Apr;3(2):101-13. PMID: 9577246.