Oleoylestrone

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

MedKoo CAT#: 529325

CAS#: 180003-17-2

Description: Oleoylestrone is an estrogen receptor agonist potentially for the treatment of obesity.

Chemical Structure

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Oleoylestrone
CAS# 180003-17-2
Instruction

Theoretical Analysis

MedKoo Cat#: 529325
Name: Oleoylestrone
CAS#: 180003-17-2
Chemical Formula: C36H54O3
Exact Mass: 534.41
Molecular Weight: 534.820
Elemental Analysis: C, 80.85; H, 10.18; O, 8.97

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: MP-101; MP101; MP 101

IUPAC/Chemical Name: (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl oleate

InChi Key: IMIPDPVHGGHVNH-YWVHRCQQSA-N

InChi Code: InChI=1S/C36H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(38)39-29-20-22-30-28(27-29)19-21-32-31(30)25-26-36(2)33(32)23-24-34(36)37/h10-11,20,22,27,31-33H,3-9,12-19,21,23-26H2,1-2H3/b11-10-/t31-,32-,33+,36+/m1/s1

SMILES Code: C[C@]1([C@](CC2)([H])[C@]3([H])CCC4=C(C=CC(OC(CCCCCCC/C=C\CCCCCCCC)=O)=C4)[C@@]3([H])CC1)C2=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: 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 534.82 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: Remesar X, Fernández-López JA, Alemany M. Oleoyl-estrone. Med Res Rev. 2012 Nov;32(6):1263-91. doi: 10.1002/med.20240. Review. PubMed PMID: 21287573.

2: Castrillejo VM, Romero MM, Esteve M, Ardévol A, Blay M, Bladé C, Arola L, Salvadó MJ. Antioxidant effects of a grapeseed procyanidin extract and oleoyl-estrone in obese Zucker rats. Nutrition. 2011 Nov-Dec;27(11-12):1172-6. doi: 10.1016/j.nut.2010.12.010. PubMed PMID: 21497054.

3: Vilà R, Cabot C, Villarreal L, Monegal A, Ayet E, Romero Mdel M, Grasa Mdel M, Esteve M, Fernández-López JA, Remesar X, Alemany M. Oleoyl-estrone is a precursor of an estrone-derived ponderostat signal. J Steroid Biochem Mol Biol. 2011 Apr;124(3-5):99-111. doi: 10.1016/j.jsbmb.2011.01.017. PubMed PMID: 21310232.

4: Strassburg S, Pfluger PT, Chaudhary N, Tso P, Tschöp MH, Anker SD, Nogueiras R, Perez-Tilve D. Action profile of the antiobesity drug candidate oleoyl-estrone in rats. Obesity (Silver Spring). 2010 Dec;18(12):2260-7. doi: 10.1038/oby.2010.53. PubMed PMID: 20339368.

5: Romero Mdel M, Vilà R, Fernández-López JA, Esteve M, Alemany M. Oleoyl-estrone increases adrenal corticosteroid synthesis gene expression in overweight male rats. Steroids. 2010 Jan;75(1):20-6. doi: 10.1016/j.steroids.2009.09.009. PubMed PMID: 19793540.

6: del Mar Romero M, Fernández-López JA, Esteve M, Alemany M. Site-related white adipose tissue lipid-handling response to oleoyl-estrone treatment in overweight male rats. Eur J Nutr. 2009 Aug;48(5):291-9. doi: 10.1007/s00394-009-0013-2. PubMed PMID: 19326039.

7: Ferrer-Lorente R, Cabot C, Fernández-López JA, Alemany M. Site-specific modulation of white adipose tissue lipid metabolism by oleoyl-estrone and/or rosiglitazone in overweight rats. Naunyn Schmiedebergs Arch Pharmacol. 2010 Apr;381(4):339-48. doi: 10.1007/s00210-010-0495-8. PubMed PMID: 20195573.

8: Romero MM, Vila R, Fernandez-Lopez JA, Esteve M, Alemany M. Influence of oleoyl-estrone treatment on circulating testosterone. Role of 17beta-hydroxysteroid dehydrogenase isoenzymes. J Physiol Pharmacol. 2009 Mar;60(1):181-90. PubMed PMID: 19439821.

9: Ferrer-Lorente R, Fernández-López JA, Alemany M, Cabot C. Short-term oral oleoyl-estrone decreases the expression of ghrelin in the rat stomach. Regul Pept. 2009 Jan 8;152(1-3):79-81. doi: 10.1016/j.regpep.2008.09.004. PubMed PMID: 18848587.

10: Serrano M, Grasa Mdel M, Janer G, Fernández-López JA, Alemany M. Oleoyl-estrone affects lipid metabolism in adrenalectomized rats treated with corticosterone through modulation of SREBP1c expression. J Steroid Biochem Mol Biol. 2009 Oct;117(1-3):15-22. doi: 10.1016/j.jsbmb.2009.06.003. PubMed PMID: 19545626.

11: García-Peláez B, Vilà R, Remesar X. Maternal treatment with oleoyl-estrone induces resistance to lipid accrual in their descendants. Obesity (Silver Spring). 2008 Oct;16(10):2223-31. doi: 10.1038/oby.2008.341. PubMed PMID: 18719652.

12: García-Peláez B, Vilà R, Remesar X. Treatment of pregnant rats with oleoyl-estrone slows down pup fat deposition after weaning. Reprod Biol Endocrinol. 2008 Jun 20;6:23. doi: 10.1186/1477-7827-6-23. PubMed PMID: 18570654; PubMed Central PMCID: PMC2459176.

13: Salas A, Noé V, Ciudad CJ, Romero MM, Remesar X, Esteve M. Short-term oleoyl-estrone treatment affects capacity to manage lipids in rat adipose tissue. BMC Genomics. 2007 Aug 28;8:292. PubMed PMID: 17725831; PubMed Central PMCID: PMC2020488.

14: del Mar Grasa M, Serrano M, Fernández-López JA, Alemany M. Corticosterone inhibits the lipid-mobilizing effects of oleoyl-estrone in adrenalectomized rats. Endocrinology. 2007 Aug;148(8):4056-63. PubMed PMID: 17510239.

15: Serrano-Muñoz M, Grasa MM, González-Martínez D, Cabot C, Fernández-López JA, Alemany M. Intestinal oleoyl-estrone esterase activity in the Wistar rat. J Endocrinol Invest. 2008 Feb;31(2):125-31. PubMed PMID: 18362503.

16: García-Peláez B, Vilà R, Remesar X. The administration of oleoyl-estrone to lactating dams induces selective changes in the normal growth pattern of their pups. Horm Metab Res. 2007 Aug;39(8):582-8. PubMed PMID: 17712723.

17: Ferrer-Lorente R, Cabot C, Fernández-López JA, Alemany M. Effects of combined oleoyl-estrone and rimonabant on overweight rats. J Pharmacol Sci. 2007 Jun;104(2):176-82. PubMed PMID: 17558182.

18: Cabot C, González-Martínez D, Fernández-López JA, Alemany M. In the rat, estrone sulphate is the main serum metabolite of oral oleoyl-estrone. J Endocrinol Invest. 2007 May;30(5):376-81. PubMed PMID: 17598968.

19: García-Peláez B, Vilà R, Remesar X. Different uptake and handling of oleoyl-estrone by fetuses and neonatal rats. Horm Metab Res. 2007 Apr;39(4):278-81. PubMed PMID: 17447166.

20: Romero MM, Esteve M, Alemany M. Combined effects of oral oleoyl-estrone and limited food intake on body composition of young overweight male rats. Int J Obes (Lond). 2006 Jul;30(7):1149-56. PubMed PMID: 16418752.