(R,R)-Tetrahydrochrysene

Chemical structure of (R,R)-Tetrahydrochrysene

(R,R)-Tetrahydrochrysene (also known as (R,R)-THC) is a synthetic, nonsteroidal compound that binds selectively to estrogen receptors (ERs). It functions as an agonist of the estrogen receptor alpha (ERα) and as an antagonist of the estrogen receptor beta (ERβ). Because of its selective receptor activity, it is primarily used in scientific research to investigate estrogen signaling pathways and the differential roles of ER subtypes in various tissues.

Chemical Properties

• IUPAC name: (5R,11R)-5,11-diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol
• Molecular formula: C₂₂H₂₄O₂
• Molecular weight: 320.43 g/mol
• CAS Number: 138090-06-9 / 221368-54-3
• Chemical class: Nonsteroidal estrogen analog
• Synonyms:

(R,R)-THC (R,R)-cis-Diethyl tetrahydro-2,8-chrysenediol (5R,11R)-5,11-diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol (R,R)-5,11-DIETHYL-5,6,11,12-TETRAHYDRO-2,8-CHRYSENEDIOL Lopac-D-8690 UNII: JDD6B8E8CW CHEMBL282489 MLS002153151

Pharmacology

(R,R)-Tetrahydrochrysene is a stereoisomer with two chiral centers, which confer its specific receptor selectivity. As a selective estrogen receptor modulator (SERM), it displays dual behavior depending on the receptor subtype it binds:

• Acts as an agonist at ERα, mimicking the action of endogenous estrogens such as estradiol.
• Acts as an antagonist at ERβ, blocking the receptor and inhibiting downstream estrogen-mediated gene expression.

This dual behavior allows researchers to dissect the roles of ERα and ERβ in biological processes, such as cell proliferation, apoptosis, metabolism, and reproductive physiology.

Mechanism of Action

(R,R)-Tetrahydrochrysene binds to the ligand-binding domain (LBD) of estrogen receptors, which induces conformational changes affecting the receptor's interaction with coactivators or corepressors. These interactions ultimately influence gene transcription and protein synthesis.

Its antagonistic activity on ERβ, contrasted with its agonist effect on ERα, makes it a powerful tool in molecular biology for identifying receptor-specific pathways and for testing hypotheses related to selective estrogen receptor modulators.

Research Applications

(R,R)-Tetrahydrochrysene is primarily used in experimental settings, particularly in:

• Endocrine research – to explore estrogen receptor function
• Cancer biology – especially in ER-positive breast cancer and prostate cancer models
• Reproductive health – to study ovarian follicle formation and estrogen-mediated processes
• Drug development – as a lead compound or control molecule in the development of novel estrogen receptor modulators

Related Compounds

• Estradiol – endogenous estrogen with non-selective ER binding
• Tamoxifen – a clinically used SERM
• Raloxifene – used in osteoporosis and breast cancer prevention
• Diethylstilbestrol – synthetic estrogen

See Also

• Estrogen receptor
• Selective estrogen receptor modulator
• Endocrine system
• Estrogens
• Hormone replacement therapy

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