689295-71-4

Basic information

• Product Name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate
• Synonyms: 2H-naphtho[2,1-c]pyran-7-carboxylic acid, 2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-9-(1-oxopropoxy)-, methyl ester, (2S,4aR,6aR,7R,9S,10aS,10bR)-
• CAS NO: 689295-71-4
• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.4902
• Mol File: 689295-71-4.mol

Chemical Properties

• Boiling Point: 573.4°C at 760 mmHg
• Flash Point: 300.6°C
• Density: 1.26g/cm³
• Vapor Pressure: 3.73E-13mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate(689295-71-4)
• EPA Substance Registry System: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate(689295-71-4)

Safety Data

• Hazardous Substances Data: 689295-71-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate is used as a pharmaceutical agent for its potential therapeutic effects. Its unique molecular structure and functional groups may contribute to its interaction with specific biological targets, such as enzymes, receptors, or ion channels, leading to modulation of cellular processes and potential treatment of various diseases.
Used in Chemical Research:
methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate is also used in chemical research as a model compound for studying the synthesis, properties, and reactivity of benzo[f]isochromene derivatives. Its complex stereochemistry and functional groups provide opportunities for investigating asymmetric synthesis, chiral recognition, and stereoselective reactions, as well as exploring the structure-activity relationships of this class of compounds.
Used in Drug Delivery Systems:
Methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(propanoyloxy)dodecahydro-2H-benzo[f]isochromene-7-carboxylate can be employed in drug delivery systems to improve the bioavailability, targeting, and therapeutic efficacy of other pharmaceutical agents. Its functional groups, such as the carboxylate group, can be utilized for conjugation to drug molecules, nanoparticles, or other carriers, enabling the development of novel drug delivery platforms.

Upstream product

• 92545-30-7 salvinorin B 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 
• 802294-64-0 propionic acid 
• 83729-01-5 salvinorin A 

Relevant articles and documents

Salvinorin A, an Active Component of the Hallucinogenic Sage Salvia divinorum Is a Highly Efficacious κ-Opioid Receptor Agonist: Structural and Functional Considerations

The diterpene salvinorin A from Salvia divinorum has recently been reported to be a high-affinity and selective κ-opioid receptor agonist (Roth et al., 2002). Salvinorin A and selected derivatives were found to be potent and efficacious agonists in severa

Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)

Salvinorin A is the only known non-nitrogenous and specific κ-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the κ-opioid receptor. Unsubstituted carbamate 9 was a potent κ-agonist (EC50 = 6.2 nM) and should be more stable than salvinorin A toward metabolic transformations. Compound 10, containing an N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed.

Development of an enzyme immunoassay using a monoclonal antibody against the psychoactive diterpenoid salvinorin A

Salvinorin A (1), the main active constituent in Salvia divinorum, is a highly selective kappa-opioid receptor agonist with hallucinogenic effects, which is regulated in several countries. In the present study, a monoclonal antibody (mAb) against 1 was prepared, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) system was developed for the detection of salvinorins. To raise mAbs against 1, salvinorin B (2) hemisuccinate was synthesized and used to prepare the immunogen 2-bovine serum albumin conjugate. This technique was used to prepare a hybridoma cell line, 3D5, which secreted a mAb that recognized 1. The mAb was shown to have specificity for 1 and other salvinorins in cross-reactivity tests. The intra-assay calibration range by icELISA using the mAb against 1 was 0.0195-0.625 μg/mL. After validating the icELISA using intra- and interassays, a recovery experiment and analysis of several plants in the family Lamiaceae, including S. divinorum, confirmed that the analytical method based on ELISA is not only simple but also precise, accurate, sensitive, and sufficiently reliable. The results indicate that icELISA is a useful tool in the identification of S. divinorum.

Opioid receptor ligands and methods for their preparation

The invention provides novel compounds of formula I: that are opioid receptor ligands. The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating diseases associated with opioid receptor function by a

SALVINORIN DERIVATIVES AND USES THEREOF

The invention features salvinorin compositions that are selective for kappa opioid receptors; methods of treating mania by using a selective kappa receptor agonist; and methods of treating mood disorders, such as depressive disorders and manic disorders,

Neoclerodane diterpenes as a novel scaffold for μ opioid receptor ligands

Structural modification of salvinorin A, the active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study a nonnitrogenous neoclerodane diterpene w