R,R-THC | CAS#138090-06-9 | estrogen receptor-β selective antagonist

MedKoo Cat#: 561320 | Name: R,R-THC

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Description:

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

R,R-THC is a estrogen receptor-β selective antagonist. R,R-THC also inhibits DHEA and DHEA metabolite transcriptional activity in ERβ-transfected cells. R,R-THC has also been shown to have neuroprotective effects against glutamate-induced death in primary rat cortical cells and mouse N29/4 hypothalamic cells.

Chemical Structure

R,R-THC

CAS#138090-06-9

Theoretical Analysis

MedKoo Cat#: 561320

Name: R,R-THC

CAS#: 138090-06-9

Chemical Formula: C22H24O2

Exact Mass: 320.1776

Molecular Weight: 320.43

Elemental Analysis: C, 82.46; H, 7.55; O, 9.99

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 785.00	2 Weeks

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Synonym

R,R-THC; R,R THC; R,RTHC

IUPAC/Chemical Name

(5R,11R)-5,11-Diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol

InChi Key

MASYAWHPJCQLSW-ZIAGYGMSSA-N

InChi Code

InChI=1S/C22H24O2/c1-3-13-9-15-11-17(23)6-8-20(15)22-14(4-2)10-16-12-18(24)5-7-19(16)21(13)22/h5-8,11-14,23-24H,3-4,9-10H2,1-2H3/t13-,14-/m1/s1

SMILES Code

OC(C=C1C[C@H]2CC)=CC=C1C3=C2C4=C(C=C(O)C=C4)C[C@H]3CC

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

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Product Data

Product Data

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 320.43 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

1: Nicholson TM, Moses MA, Uchtmann KS, Keil KP, Bjorling DE, Vezina CM, Wood RW, Ricke WA. Estrogen receptor-α is a key mediator and therapeutic target for bladder complications of benign prostatic hyperplasia. J Urol. 2015 Feb;193(2):722-9. doi: 10.1016/j.juro.2014.08.093. Epub 2014 Aug 25. PubMed PMID: 25167991; PubMed Central PMCID: PMC4305478. 2: Jung US, Jeong KJ, Kang JK, Yi K, Shin JH, Seo HS, Kim T, Kim SH, Hur JY. Effects of estrogen receptor α and β on the expression of visfatin and retinol-binding protein 4 in 3T3-L1 adipocytes. Int J Mol Med. 2013 Sep;32(3):723-8. doi: 10.3892/ijmm.2013.1440. Epub 2013 Jul 12. PubMed PMID: 23857051. 3: Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA. DHEA metabolites activate estrogen receptors alpha and beta. Steroids. 2013 Jan;78(1):15-25. doi: 10.1016/j.steroids.2012.10.002. Epub 2012 Nov 2. PubMed PMID: 23123738; PubMed Central PMCID: PMC3529809. 4: Miró AM, Sastre-Serra J, Pons DG, Valle A, Roca P, Oliver J. 17β-Estradiol regulates oxidative stress in prostate cancer cell lines according to ERalpha/ERbeta ratio. J Steroid Biochem Mol Biol. 2011 Feb;123(3-5):133-9. doi: 10.1016/j.jsbmb.2010.12.004. Epub 2010 Dec 21. PubMed PMID: 21172438. 5: Norata GD, Cattaneo P, Poletti A, Catapano AL. The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits tumor necrosis factor alpha and lipopolysaccharide induced inflammatory response in human endothelial cells and in mice aorta. Atherosclerosis. 2010 Sep;212(1):100-6. doi: 10.1016/j.atherosclerosis.2010.05.015. Epub 2010 May 19. PubMed PMID: 20557886. 6: Townsend EA, Thompson MA, Pabelick CM, Prakash YS. Rapid effects of estrogen on intracellular Ca2+ regulation in human airway smooth muscle. Am J Physiol Lung Cell Mol Physiol. 2010 Apr;298(4):L521-30. doi: 10.1152/ajplung.00287.2009. Epub 2010 Jan 22. PubMed PMID: 20097735; PubMed Central PMCID: PMC2853343. 7: Xia Y, Xing JZ, Krukoff TL. Neuroprotective effects of R,R-tetrahydrochrysene against glutamate-induced cell death through anti-excitotoxic and antioxidant actions involving estrogen receptor-dependent and -independent pathways. Neuroscience. 2009 Aug 18;162(2):292-306. doi: 10.1016/j.neuroscience.2009.04.068. Epub 2009 May 3. PubMed PMID: 19410635. 8: Yi KW, Shin JH, Seo HS, Lee JK, Oh MJ, Kim T, Saw HS, Kim SH, Hur JY. Role of estrogen receptor-alpha and -beta in regulating leptin expression in 3T3-L1 adipocytes. Obesity (Silver Spring). 2008 Nov;16(11):2393-9. doi: 10.1038/oby.2008.389. Epub 2008 Aug 21. PubMed PMID: 18719660. 9: Zaitseva M, Yue DS, Katzenellenbogen JA, Rogers PA, Gargett CE. Estrogen receptor-alpha agonists promote angiogenesis in human myometrial microvascular endothelial cells. J Soc Gynecol Investig. 2004 Dec;11(8):529-35. PubMed PMID: 15582497. 10: Harrington WR, Sheng S, Barnett DH, Petz LN, Katzenellenbogen JA, Katzenellenbogen BS. Activities of estrogen receptor alpha- and beta-selective ligands at diverse estrogen responsive gene sites mediating transactivation or transrepression. Mol Cell Endocrinol. 2003 Aug 29;206(1-2):13-22. PubMed PMID: 12943986. 11: Bowe J, Li XF, Sugden D, Katzenellenbogen JA, Katzenellenbogen BS, O'Byrne KT. The effects of the phytoestrogen, coumestrol, on gonadotropin-releasing hormone (GnRH) mRNA expression in GT1-7 GnRH neurones. J Neuroendocrinol. 2003 Feb;15(2):105-8. PubMed PMID: 12535152. 12: Somponpun S, Sladek CD. Role of estrogen receptor-beta in regulation of vasopressin and oxytocin release in vitro. Endocrinology. 2002 Aug;143(8):2899-904. PubMed PMID: 12130554. 13: Nuedling S, Karas RH, Mendelsohn ME, Katzenellenbogen JA, Katzenellenbogen BS, Meyer R, Vetter H, Grohé C. Activation of estrogen receptor beta is a prerequisite for estrogen-dependent upregulation of nitric oxide synthases in neonatal rat cardiac myocytes. FEBS Lett. 2001 Aug 3;502(3):103-8. PubMed PMID: 11583108. 14: Kraichely DM, Sun J, Katzenellenbogen JA, Katzenellenbogen BS. Conformational changes and coactivator recruitment by novel ligands for estrogen receptor-alpha and estrogen receptor-beta: correlations with biological character and distinct differences among SRC coactivator family members. Endocrinology. 2000 Oct;141(10):3534-45. PubMed PMID: 11014206. 15: Sun J, Meyers MJ, Fink BE, Rajendran R, Katzenellenbogen JA, Katzenellenbogen BS. Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta. Endocrinology. 1999 Feb;140(2):800-4. PubMed PMID: 9927308.