(R,R)-THC

Cat. No. 1990 8 Citations Submit a Review Datasheet / COA / SDS

Pricing	Availability		Qty

Description: Potent subtype-selective ligand; ERα agonist/ERβ antagonist

Chemical Name: (R,R)-5,11-Diethyl-5,6,11,12-tetrahydro-2,8-chrysenediol

Purity: ≥98% (HPLC)

Datasheet

Citations (8)

Reviews

Pathways (1)

Biological Activity Technical Data Solubility Calculators Datasheets References

Biological Activity for (R,R)-THC

(R,R)-THC is a non-steroidal, selective estrogen receptor ligand. (R,R)-THC is an agonist at ERα receptor (K_i = 9.0 nM) and antagonist at ERβ receptor (K_i = 3.6 nM).

Technical Data for (R,R)-THC

M. Wt	320.42
Formula	C₂₂H₂₄O₂
Storage	Store at -20°C
Purity	≥98% (HPLC)
CAS Number	138090-06-9
PubChem ID	446849
InChI Key	MASYAWHPJCQLSW-ZIAGYGMSSA-N
Smiles	OC3=CC=C(C(C[C@H]4CC)=C3)C2=C4C1=CC=C(O)C=C1C[C@H]2CC

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for (R,R)-THC

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	32.04	100
	ethanol	32.04	100

Preparing Stock Solutions for (R,R)-THC

The following data is based on the product molecular weight 320.42. 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	3.12 mL	15.6 mL	31.21 mL
5 mM	0.62 mL	3.12 mL	6.24 mL
10 mM	0.31 mL	1.56 mL	3.12 mL
50 mM	0.06 mL	0.31 mL	0.62 mL

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Product Datasheets for (R,R)-THC

Certificate of Analysis / Product Datasheet

Safety Datasheet

References for (R,R)-THC

References are publications that support the biological activity of the product.

Sun et al (1999) Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-α or estrogen receptor-β. Endocrinology 140 800 PMID: 9927308

Kraichely et al (2000) Conformational changes and coactivator recruitment by novel ligands for estrogen receptor-α and estrogen receptor-β: correlations with biological character and distinct differences among SRC coactivator family members. Endocrinology 141 3534 PMID: 11014206

Meyers et al (1999) Estrogen receptor subtype-selective ligands: asymmetric synthesis and biological evaluation of cis- and trans-5,11-dialkyl- 5,6,11, 12-tetrahydrochrysenes. J.Med.Chem. 42 2456 PMID: 10395487

If you know of a relevant reference for (R,R)-THC, please let us know.

View Related Products by Target

Estrogen and Related Receptors

Keywords: (R,R)-THC, (R,R)-THC supplier, Potent, subtype, selective, ligands, Erα, Eralpha, agonists, ERβ, ERbeta, antagonists, ER, ERR, Estrogen, Receptors, and, Related, 1990, Tocris Bioscience

8 Citations for (R,R)-THC

Citations are publications that use Tocris products. Selected citations for (R,R)-THC include:

Wang et al (2015) Bu-Shen-Ning-Xin decoction: inhibition of osteoclastogenesis by abrogation of the RANKL-induced NFATc1 and NF-κB signaling pathways via selective estrogen receptor α. Drug Des Devel Ther 9 3755 PMID: 26229438

Guo et al (2011) Baicalin, a flavone, induces the differentiation of cultured osteoblasts: an action via the Wnt/beta-catenin signaling pathway. J Biol Chem 286 27882 PMID: 21652696

Vona et al (2019) Functional Estrogen Receptors of Red Blood Cells. Do They Influence Intracellular Signaling? Cell Physiol Biochem 53 186 PMID: 31278696

Li et al (2013) Inhibition of fatty acid amide hydrolase activates Nrf2 signalling and induces heme oxygenase 1 transcription in breast cancer cells. Br J Pharmacol 170 489 PMID: 23347118

Simpkins et al (2012) Src Inhibition with saracatinib reverses fulves. resistance in ER-positive ovarian cancer models in vitro and in vivo. Clin Cancer Res 18 5911 PMID: 22896656

Xing et al (2012) Estrogen modulates NFκB signaling by enhancing IκBα levels and blocking p65 binding at the promoters of inflammatory genes via estrogen receptor-β. PLoS One 7 e36890 PMID: 22723832

Nicholson et al (2015) Estrogen receptor-α is a key mediator and therapeutic target for bladder complications of benign prostatic hyperplasia. PLoS One 193 722 PMID: 25167991

Kola et al The orexigenic effect of ghrelin is mediated through central activation of the endogenous cannabinoid system. PLoS One 3 e1797 PMID: 18335063

Do you know of a great paper that uses (R,R)-THC from Tocris? Please let us know.

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Pathways for (R,R)-THC

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.