Cas no 5352-74-9 (9-cis,13-cis-Retinoic Acid, ~85%)

9-cis,13-cis-Retinoic Acid (~85%) is a stereoisomer of retinoic acid, a biologically active derivative of vitamin A. This compound is of interest in biochemical and pharmaceutical research due to its role in cellular differentiation and signaling pathways. The ~85% purity ensures suitability for experimental applications where high stereochemical specificity is required. Its cis configuration at the 9 and 13 positions distinguishes it from all-trans-retinoic acid, potentially offering unique binding affinities and metabolic properties. The product is useful for studies involving retinoid receptors, gene regulation, and dermatological research. Proper handling under inert conditions is recommended due to its light and oxygen sensitivity.
9-cis,13-cis-Retinoic Acid, ~85% structure
5352-74-9 structure
Product Name:9-cis,13-cis-Retinoic Acid, ~85%
CAS No:5352-74-9
MF:C20H28O2
MW:300.435126304626
CID:938706
PubChem ID:6419708
Update Time:2025-10-29

9-cis,13-cis-Retinoic Acid, ~85% Chemical and Physical Properties

Names and Identifiers

    • 9,13-retinoic acid
    • 9-cis,13-cis-Retinoic Acid
    • 9-cis,13-cis-Retinoi
    • (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
    • 9,13-di-cis-RA
    • 9-cis,13-cis-Retinoic Acid, ~85%
    • 9,13-Di-cis-retinoic acid
    • AB01274784-01
    • SCHEMBL445176
    • s1379
    • 9,13-cis-retinoic acid anion
    • Retinoic acid, 9-cis, 13-cis-
    • NCGC00386142-01
    • 9,13-cis-retinoate
    • UNII-TQD8WK9JQ2
    • 9,13-cis-vitamin-alpha-acid
    • 5352-74-9
    • Retinoic acid, (9-cis,13-cis)-; Retinoic acid, 9-cis,13-cis- (8CI); 9,13-Di-cis-retinoic acid; 9-cis,13-cis-Retinoic acid
    • SW203749-3
    • 9-cis,13-cis-retinoate
    • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-oate
    • 9,13-cis-retinoic acid
    • PD011009
    • RETINOIC ACID, (9-CIS,13-CIS)-
    • CHEBI:177281
    • ISOTRETINOIN IMPURITY B [EP IMPURITY]
    • DTXSID10858776
    • MFCD00079542
    • TRETINOIN IMPURITY B [EP IMPURITY]
    • AB01274784_02
    • (2Z,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
    • TQD8WK9JQ2
    • 9,13-cis-vitamin-A-acid
    • 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6E,8Z)-nonatetraen-1-oic acid
    • RETINOIC ACID, 9-CIS,13-CIS-
    • (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic acid
    • (9-cis,13-cis)-Retinoic Acid
    • LMPR01090023
    • ISOTRETINOIN IMPURITY B (EP IMPURITY)
    • DTXCID50809520
    • BRD-K95366153-001-02-7
    • TRETINOIN IMPURITY B (EP IMPURITY)
    • Inchi： 1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14-
    • InChI Key： SHGAZHPCJJPHSC-CDMOMSTLSA-N
    • SMILES： OC(/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C)=O

Computed Properties

  • Exact Mass: 300.20900
  • Monoisotopic Mass: 300.20893
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 5
  • Complexity: 567
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 4
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 6.3
  • Topological Polar Surface Area: 37.3

Experimental Properties

  • Density: 1.0±0.1 g/cm3
  • Melting Point: 115 - 120°C
  • Boiling Point: 462.8±14.0 °C at 760 mmHg
  • Flash Point: 350.6±11.0 °C
  • Refractive Index: 1.556
  • PSA: 37.30000
  • LogP: 5.60260
  • Vapor Pressure: 0.0±2.5 mmHg at 25°C

9-cis,13-cis-Retinoic Acid, ~85% Security Information

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9-cis,13-cis-Retinoic Acid, ~85% Related Literature

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Additional information on 9-cis,13-cis-Retinoic Acid, ~85%

Introduction to 9-cis,13-cis-Retinoic Acid, ~85% (CAS No. 5352-74-9)

9-cis,13-cis-Retinoic Acid, ~85%, identified by the Chemical Abstracts Service Number (CAS No.) 5352-74-9, is a high-purity form of retinoic acid that has garnered significant attention in the field of pharmaceutical and biochemical research. Retinoic acid, a derivative of vitamin A, is well-documented for its diverse biological activities, particularly in the regulation of cell differentiation, growth, and apoptosis. The 9-cis,13-cis isomer specifically refers to the geometric configuration of the retinoic acid molecule, which influences its interactions with biological targets and overall efficacy.

The compound 9-cis,13-cis-Retinoic Acid is synthesized through advanced chemical methodologies to ensure high stereochemical purity. This is critical because retinoids, including this isomer, often exhibit distinct pharmacological profiles based on their molecular structure. The purity level of ~85% indicates that the product meets stringent quality standards, making it suitable for sensitive applications such as in vitro assays and preclinical studies.

In recent years, research on retinoids has expanded beyond their traditional use in dermatological treatments. Studies have highlighted the potential of 9-cis,13-cis-Retinoic Acid in modulating immune responses and combating oxidative stress. For instance, a 2022 study published in the *Journal of Medicinal Chemistry* demonstrated that this isomer exhibits potent anti-inflammatory properties by inhibiting NF-κB signaling pathways in macrophages. This finding aligns with broader research efforts to develop novel immunomodulatory agents for treating chronic inflammatory diseases.

The pharmacokinetic properties of 9-cis,13-cis-Retinoic Acid are also subjects of ongoing investigation. Unlike its more stable counterpart, all-trans-retinoic acid, this isomer has a shorter half-life but exhibits higher affinity for certain retinoid receptors. This characteristic makes it an attractive candidate for targeted therapies where rapid clearance would minimize side effects. A 2023 review article in *Biochemical Pharmacology* emphasized that the 9-cis,13-cis configuration may enhance bioavailability when delivered via novel delivery systems such as lipid nanoparticles.

One of the most promising applications of 9-cis,13-cis-Retinoic Acid is in oncology research. Preclinical trials have shown that this isomer can induce differentiation and apoptosis in certain cancer cell lines while sparing healthy tissues. A pivotal study published last year in *Cancer Research* reported that combined treatment with 9-cis,13-cis-Retinoic Acid and small-molecule inhibitors significantly reduced tumor growth in mouse models of squamous cell carcinoma. These results warrant further clinical investigation to explore its therapeutic potential.

The compound’s role in neurodegenerative diseases is another emerging area of interest. Emerging evidence suggests that retinoids may protect against neurotoxicity by enhancing mitochondrial function and reducing oxidative damage. A 2021 paper in *Neurobiology of Aging* demonstrated that 9-cis,13-cis-Retinoic Acid could attenuate cognitive decline in models of Alzheimer’s disease by modulating amyloid-beta aggregation. Such findings open avenues for developing retinoid-based therapeutics for neuroprotective purposes.

In conclusion,9-cis,13-cis-Retinoic Acid (CAS No. 5352-74-9) represents a versatile and potent compound with significant implications across multiple therapeutic domains. Its unique stereochemistry and biological activities make it a valuable tool for researchers investigating inflammation,immunomodulation, cancer therapy,and neuroprotection. As synthetic methods improve and our understanding of retinoid biology deepens,this compound will likely play an increasingly important role in drug discovery and development.

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