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38030-57-8,MFCD00870472
Catalog No.:AA00C9AG

38030-57-8 | (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid

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1mg
≥95%
in stock  
$80.00   $56.00
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5mg
96%
in stock  
$352.00   $247.00
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10mg
96%
in stock  
$529.00   $370.00
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25mg
≥95%
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$985.00   $689.00
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50mg
96%
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00C9AG
Chemical Name:
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
CAS Number:
38030-57-8
Molecular Formula:
C20H26O3
Molecular Weight:
314.4186
MDL Number:
MFCD00870472
SMILES:
C/C(=C\C=C\C(=C\C(=O)O)\C)/C=C/C1=C(C)C(=O)CCC1(C)C
Properties
Properties
 
BP:
509.9±29.0 °C(Predicted)  
Form:
Solid  
MP:
175-179 °C  

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  

Downstream Synthesis Route

[1]SyntheticCommunications,1987,vol.17,p.419-430

Literature

Title: Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids.

Journal: Molecular pharmacology 20150301

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: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system.

Journal: Pharmacogenetics and genomics 20070301

Title: Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells.

Journal: Archives of biochemistry and biophysics 20061101

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: The control of morphogen signalling: regulation of the synthesis and catabolism of retinoic acid in the developing embryo.

Journal: Developmental biology 20050901

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: Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents.

Journal: Journal of medicinal chemistry 20050324

Title: All-trans retinoic acid is a ligand for the orphan nuclear receptor ROR beta.

Journal: Nature structural biology 20031001

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: HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A.

Journal: Journal of lipid research 20020701

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: Identification of human cytochrome P450 isoforms that contribute to all-trans-retinoic acid 4-hydroxylation.

Journal: Biochemical pharmacology 20000815

Title: Initial retinoid requirement for early avian development coincides with retinoid receptor coexpression in the precardiac fields and induction of normal cardiovascular development.

Journal: Developmental dynamics : an official publication of the American Association of Anatomists 19981001

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

Title: Topletz AR, et al. Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41.

Title: Stahl W, et al. 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8.

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SDS
Tags:38030-57-8 Molecular Formula|38030-57-8 MDL|38030-57-8 SMILES|38030-57-8 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid