2-OHE1 | CAS#362-06-1 | MCF-7 proliferation inhibitor

2-OHE1
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 464822

CAS#: 362-06-1

Description: 2-hydroxy Estrone (2-OHE1) is an active metabolite of the endogenous estrogen estrone. It is formed from estrone primarily by the cytochrome P450 (CYP) isoforms CYP1A2, CYP1A1, and CYP1B1 and metabolized to 2-methoxy estrone by catechol-O-methyltransferase (COMT). 2-hydroxy Estrone (10 µM) inhibits the proliferation of estrogen receptor-positive MCF-7, but not estrogen receptor-negative MDA-MB-231, breast cancer cells cultured with the COMT inhibitor quinalizarin. It inhibits iron-ADP-adriamycin complex-induced lipid peroxidation of liposomes prepared from rat liver microsomes (IC50 = 2.7 µM).

Chemical Structure

2-OHE1

CAS# 362-06-1

Instruction

Theoretical Analysis

MedKoo Cat#: 464822
Name: 2-OHE1
CAS#: 362-06-1
Chemical Formula: C18H22O3
Exact Mass: 286.16
Molecular Weight: 286.371
Elemental Analysis: C, 75.50; H, 7.74; O, 16.76

Price and Availability

Size	Price	Availability
1mg	USD 450	2 Weeks
5mg	USD 1350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 2-OHE1; 2OHE1; 2 OHE1; 2-hydroxy Estrone; 2 hydroxy Estrone; Catecholestrone; 2-hydroxy E1; 2 hydroxy E1;

IUPAC/Chemical Name: (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one

InChi Key: SWINWPBPEKHUOD-JPVZDGGYSA-N

InChi Code: InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

SMILES Code: C[C@]12[C@]([H])([C@]3([C@@]([H])(C4=CC(O)=C(C=C4CC3)O)CC2)[H])CCC1=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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	104.76
	DMSO	30.0	104.76
	Ethanol	30.0	104.76
	Ethanol:PBS (pH 7.2) (1:2)	0.3	1.15

Preparing Stock Solutions

The following data is based on the product molecular weight 286.37 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:
In vitro protocol:
In vivo protocol:

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1: Mahabir S, Pfeiffer R, Xu X, Baer DJ, Taylor PR. Effects of low-to-moderate alcohol supplementation on urinary estrogen metabolites in postmenopausal women in a controlled feeding study. Cancer Med. 2017 Oct;6(10):2419-2423. doi: 10.1002/cam4.1153. Epub 2017 Sep 6. PMID: 28879665; PMCID: PMC5633545.

2: Zhao F, Wang X, Wang Y, Zhang J, Lai R, Zhang B, Zhou X. The function of uterine UDP-glucuronosyltransferase 1A8 (UGT1A8) and UDP-glucuronosyltransferase 2B7 (UGT2B7) is involved in endometrial cancer based on estrogen metabolism regulation. Hormones (Athens). 2020 Sep;19(3):403-412. doi: 10.1007/s42000-020-00213-x. Epub 2020 Jun 26. PMID: 32592099.

3: Carroll-Turpin M, Hebert V, Chotibut T, Wensler H, Krentzel D, Varner KJ, Burn BR, Chen YF, Abreo F, Dugas TR. 4,4'-Methylenedianiline Alters Serotonergic Transport in a Novel, Sex-Specific Model of Pulmonary Arterial Hypertension in Rats. Toxicol Sci. 2015 Sep;147(1):235-45. doi: 10.1093/toxsci/kfv126. Epub 2015 Jun 26. PMID: 26116029; PMCID: PMC4731411.

4: Dikshit A, Gomes Filho MA, Eilati E, McGee S, Small C, Gao C, Klug T, Hales DB. Flaxseed reduces the pro-carcinogenic micro-environment in the ovaries of normal hens by altering the PG and oestrogen pathways in a dose-dependent manner. Br J Nutr. 2015 May 14;113(9):1384-95. doi: 10.1017/S000711451500029X. Epub 2015 Apr 8. PMID: 25850566; PMCID: PMC4445837.

5: Ruan X, Seeger H, Wallwiener D, Huober J, Mueck AO. The ratio of the estradiol metabolites 2-hydroxyestrone (2-OHE1) and 16α-hydroxyestrone (16-OHE1) may predict breast cancer risk in postmenopausal but not in premenopausal women: two case-control studies. Arch Gynecol Obstet. 2015 May;291(5):1141-6. doi: 10.1007/s00404-014-3512-1. Epub 2014 Oct 16. PMID: 25318606.

6: Arslan AA, Koenig KL, Lenner P, Afanasyeva Y, Shore RE, Chen Y, Lundin E, Toniolo P, Hallmans G, Zeleniuch-Jacquotte A. Circulating estrogen metabolites and risk of breast cancer in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2014 Jul;23(7):1290-7. doi: 10.1158/1055-9965.EPI-14-0009. Epub 2014 Apr 27. PMID: 24769889; PMCID: PMC4082442.

7: Chow HH, Garland LL, Heckman-Stoddard BM, Hsu CH, Butler VD, Cordova CA, Chew WM, Cornelison TL. A pilot clinical study of resveratrol in postmenopausal women with high body mass index: effects on systemic sex steroid hormones. J Transl Med. 2014 Aug 14;12:223. doi: 10.1186/s12967-014-0223-0. PMID: 25115686; PMCID: PMC4243716.

8: Zhao H, Jiang Y, Liu Y, Yun C, Li L. Endogenous estrogen metabolites as biomarkers for endometrial cancer via a novel method of liquid chromatography- mass spectrometry with hollow fiber liquid-phase microextraction. Horm Metab Res. 2015 Feb;47(2):158-64. doi: 10.1055/s-0034-1371865. Epub 2014 Apr 10. PMID: 24722971.

9: Telang N, Li G, Sepkovic D, Bradlow HL, Wong GY. Comparative efficacy of extracts from Lycium barbarum bark and fruit on estrogen receptor positive human mammary carcinoma MCF-7 cells. Nutr Cancer. 2014;66(2):278-84. doi: 10.1080/01635581.2014.864776. Epub 2013 Dec 30. PMID: 24377707.

10: Smith AJ, Phipps WR, Thomas W, Schmitz KH, Kurzer MS. The effects of aerobic exercise on estrogen metabolism in healthy premenopausal women. Cancer Epidemiol Biomarkers Prev. 2013 May;22(5):756-64. doi: 10.1158/1055-9965.EPI-12-1325. PMID: 23652373; PMCID: PMC3648856.

11: Peng J, Xu X, Mace BE, Vanderveer LA, Workman LR, Slifker MJ, Sullivan PM, Veenstra TD, Clapper ML. Estrogen metabolism within the lung and its modulation by tobacco smoke. Carcinogenesis. 2013 Apr;34(4):909-15. doi: 10.1093/carcin/bgs402. Epub 2012 Dec 31. PMID: 23276798; PMCID: PMC3616670.

12: Ayari I, Fedeli U, Saguem S, Hidar S, Khlifi S, Pavanello S. Role of CYP1A2 polymorphisms in breast cancer risk in women. Mol Med Rep. 2013 Jan;7(1):280-6. doi: 10.3892/mmr.2012.1164. Epub 2012 Nov 1. PMID: 23128882.

13: Mackey RH, Fanelli TJ, Modugno F, Cauley JA, McTigue KM, Brooks MM, Chlebowski RT, Manson JE, Klug TL, Kip KE, Curb JD, Kuller LH. Hormone therapy, estrogen metabolism, and risk of breast cancer in the Women's Health Initiative Hormone Therapy Trial. Cancer Epidemiol Biomarkers Prev. 2012 Nov;21(11):2022-32. doi: 10.1158/1055-9965.EPI-12-0759. Epub 2012 Aug 29. PMID: 22933427; PMCID: PMC3493689.

14: Dallal CM, Stone RA, Cauley JA, Ness RB, Vogel VG, Fentiman IS, Fowke JH, Krogh V, Loft S, Meilahn EN, Muti P, Olsen A, Overvad K, Sieri S, Tjønneland A, Ursin G, Wellejus A, Taioli E. Urinary estrogen metabolites and breast cancer: a combined analysis of individual level data. Int J Biol Markers. 2013 Apr 23;28(1):3-16. doi: 10.5301/JBM.2012.9353. PMID: 22865302.

15: Telang NT, Li G, Sepkovic DW, Bradlow HL, Wong GY. Anti-proliferative effects of Chinese herb Cornus officinalis in a cell culture model for estrogen receptor-positive clinical breast cancer. Mol Med Rep. 2012 Jan;5(1):22-8. doi: 10.3892/mmr.2011.617. Epub 2011 Oct 4. PMID: 21971582.

16: Zeleniuch-Jacquotte A, Shore RE, Afanasyeva Y, Lukanova A, Sieri S, Koenig KL, Idahl A, Krogh V, Liu M, Ohlson N, Muti P, Arslan AA, Lenner P, Berrino F, Hallmans G, Toniolo P, Lundin E. Postmenopausal circulating levels of 2- and 16α-hydroxyestrone and risk of endometrial cancer. Br J Cancer. 2011 Oct 25;105(9):1458-64. doi: 10.1038/bjc.2011.381. Epub 2011 Sep 27. PMID: 21952628; PMCID: PMC3241553.

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