Cas no 92692-39-2 (Amorphadiene)

Amorphadiene is a sesquiterpene compound that serves as a key intermediate in the biosynthesis of artemisinin, an important antimalarial agent. It is produced via the mevalonate pathway in engineered microbial systems, such as Saccharomyces cerevisiae or Escherichia coli, through the action of amorphadiene synthase (ADS). The compound’s high volatility and hydrophobic nature make it suitable for extraction and purification via gas chromatography or organic solvent-based methods. Its primary advantage lies in its role as a precursor for semi-synthetic artemisinin, enabling scalable and cost-effective production of antimalarial therapeutics. Additionally, amorphadiene’s structural versatility makes it a valuable scaffold for further chemical modifications in pharmaceutical and biotechnological applications.
Amorphadiene structure
Amorphadiene structure
Product Name:Amorphadiene
CAS No:92692-39-2
MF:C15H24
MW:204.351064682007
CID:2067785
PubChem ID:11052747
Update Time:2025-05-27

Amorphadiene Chemical and Physical Properties

Names and Identifiers

    • 1beta,6beta,7beta,10alphaH-cadina-4,11-diene
    • 4,11-amorphadiene
    • amorpha-4,11-diene
    • amorpha4,11-diene
    • amorphadiene
    • (1R,4R,4aS,8aR)-4,7-dimethyl-1-prop-1-en-2-yl-1,2,3,4,4a,5,6,8a-octahydronaphthalene
    • HMTAHNDPLDKYJT-CBBWQLFWSA-N
    • (-)-Amorpha-4,11-diene
    • (+)-amorpha-4,11-diene
    • DTXSID50239106
    • CHEBI:52026
    • LMPR0103330005
    • SJA
    • Q4747721
    • (1R,4R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4,7-dimethyl-1-1-methylethenyl)naphthalene
    • XA164865
    • (1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
    • 92692-39-2
    • Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethenyl)-, (1R-(1alpha,4beta,4abeta.,8abeta.))-
    • Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethenyl)-, [1R-(1.alpha.,4.beta.,4abeta.,8abeta.)]-
    • Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethenyl)-, (1R,4R,4aS,8aR)-; Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethenyl)-, [1R-(1a,4ss,4ass,8ass)]-; (1R,4R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4,7-dimethyl-1-(1-methylethenyl)naphthalene; (-)-Amorpha-4,11-diene; Amorpha-4,11-diene; Amorphadiene
    • Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4,7-dimethyl-1-(1-methylethenyl)-, (1R,4R,4aS,8aR)-
    • CS-0640859
    • DTXCID30161597
    • 486452-24-8
    • (1R,4R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-4,7-dimethyl-1-(1-methylethenyl)naphthalene
    • Amorphadiene
    • Inchi: 1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9,12-15H,1,5-8H2,2-4H3/t12-,13+,14+,15-/m1/s1
    • InChI Key: HMTAHNDPLDKYJT-CBBWQLFWSA-N
    • SMILES: [C@@H]12CCC(C)=C[C@@H]1[C@H](C(=C)C)CC[C@H]2C

Computed Properties

  • Exact Mass: 204.187800766g/mol
  • Monoisotopic Mass: 204.187800766g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 284
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 5.1
  • Topological Polar Surface Area: 0?2

Amorphadiene Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
A634365-1mg
Amorphadiene
92692-39-2
1mg
$ 167.00 2023-04-19
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$ 356.00 2023-04-19
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$ 640.00 2023-04-19
TRC
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$ 1217.00 2023-04-19
A2B Chem LLC
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$283.00 2024-07-18
A2B Chem LLC
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$462.00 2024-07-18
A2B Chem LLC
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$1286.00 2024-07-18

Additional information on Amorphadiene

H-Cadina-4,11-Diene: A Comprehensive Overview

H-Cadina-4,11-diene, also known by its CAS registry number 92692-39-2, is a terpenoid compound that has garnered significant attention in the field of biomedicine due to its diverse biological activities. This naturally occurring compound belongs to the cadinaane family of sesquiterpenes, which are known for their complex structures and potent bioactive properties.

The structure of H-cadina-4,11-diene is characterized by a unique arrangement of beta, alpha, and gamma hydroxyl groups, along with conjugated double bonds that contribute to its antioxidant and anti-inflammatory potential. These structural features make it a promising candidate for drug development, particularly in the treatment of chronic diseases such as cancer, diabetes, and neurodegenerative disorders.

Recent studies have highlighted the compound's ability to modulate cell signaling pathways, including the MAPK and PI3K/AKT pathways, which are often dysregulated in cancer cells. This modulation suggests that H-cadina-4,11-diene may have anticancer properties, potentially offering a novel therapeutic approach for various malignancies.

Furthermore, research into the neuroprotective effects of this compound has shown promising results in preclinical models of Alzheimer's disease. By inhibiting beta-amyloid aggregation and reducing oxidative stress, H-cadina-4,11-diene demonstrates potential as a dementia treatment. These findings underscore the importance of further investigating its mechanisms of action in neural systems.

Another area of interest is the compound's role in inflammation regulation. Through interaction with COX-2 and iNOS enzymes, H-cadina-4,11-diene exhibits anti-inflammatory activity, which could be harnessed for treating inflammatory bowel diseases or arthritis. This dual action on both inflammation and cell proliferation makes it a versatile candidate for multifunctional drugs.

Preclinical trials have also explored the toxicological profile of H-cadina-4,11-diene, revealing minimal adverse effects at therapeutic doses. This safety profile, combined with its potent bioactivities, positions it as a lead compound for drug development in several therapeutic areas.

Finally, ongoing research is focusing on optimizing the bioavailability and pharmacokinetics of H-cadina-4,11-diene to enhance its efficacy. By employing advanced drug delivery systems, scientists aim to maximize the therapeutic potential of this compound while minimizing systemic side effects.

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