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71748-58-8,MFCD00870452
Catalog No.:AA0062DS

71748-58-8 | 4-Keto 13-cis-Retinoic Acid

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1mg
≥98%
in stock  
$99.00   $69.00
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5mg
≥98%
in stock  
$308.00   $215.00
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10mg
≥98%
in stock  
$562.00   $393.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0062DS
Chemical Name:
4-Keto 13-cis-Retinoic Acid
CAS Number:
71748-58-8
Molecular Formula:
C20H26O3
Molecular Weight:
314.4186
MDL Number:
MFCD00870452
SMILES:
CC(=CC=CC(=CC(=O)O)C)/C=C/C1=C(C)C(=O)CCC1(C)C
Properties
Properties
 
Form:
Solid  
MP:
>143°C (dec.)  

Computed Properties
 
Complexity:
638  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
4  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
4.8  

Literature

Title: Metabolic characteristics of 13-cis-retinoic acid (isotretinoin) and anti-tumour activity of the 13-cis-retinoic acid metabolite 4-oxo-13-cis-retinoic acid in neuroblastoma.

Journal: British journal of pharmacology 20141201

Title: Detection of retinoic acid receptor agonistic activity and identification of causative compounds in municipal wastewater treatment plants in Japan.

Journal: Environmental toxicology and chemistry 20120901

Title: Role of UDP-glucuronosyltransferase isoforms in 13-cis retinoic acid metabolism in humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100701

Title: Metabolism and regulation of gene expression by 4-oxoretinol versus all-trans retinoic acid in normal human mammary epithelial cells.

Journal: Journal of cellular physiology 20090901

Title: The metabolism and pharmacokinetics of isotretinoin in patients with acne and rosacea are not influenced by ethanol.

Journal: The British journal of dermatology 20090901

Title: Sequential RARbeta and alpha signalling in vivo can induce adult forebrain neural progenitor cells to differentiate into neurons through Shh and FGF signalling pathways.

Journal: Developmental biology 20090215

Title: Retinoids have differing efficacies on alveolar regeneration in a dexamethasone-treated mouse.

Journal: American journal of respiratory cell and molecular biology 20060801

Title: A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid.

Journal: Molecular endocrinology (Baltimore, Md.) 20060701

Title: Method to determine 4-oxo-retinoic acids, retinoic acids and retinol in serum and cell extracts by liquid chromatography/diode-array detection atmospheric pressure chemical ionisation tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro.

Journal: The Journal of investigative dermatology 20050701

Title: Homozygous deletion of the CRABPI gene in AB1 embryonic stem cells results in increased CRABPII gene expression and decreased intracellular retinoic acid concentration.

Journal: Archives of biochemistry and biophysics 20030315

Title: Retinol metabolism and lecithin:retinol acyltransferase levels are reduced in cultured human prostate cancer cells and tissue specimens.

Journal: Cancer research 20020315

Title: Reduced levels of retinyl esters and vitamin A in human renal cancers.

Journal: Cancer research 20010315

Title: Granulocytic differentiation of human NB4 promyelocytic leukemia cells induced by all-trans retinoic acid metabolites.

Journal: Cancer research 20010115

Title: Ethanol enhances retinoic acid metabolism into polar metabolites in rat liver via induction of cytochrome P4502E1.

Journal: Gastroenterology 20010101

Title: Generation of radical oxygen species by neural crest cells treated in vitro with isotretinoin and 4-oxo-isotretinoin.

Journal: Journal of craniofacial genetics and developmental biology 19900101

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