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471-74-9-Sandaracopimaric acid Sandaracopimaric acid

Sandaracopimaric acid

For research use only. Not for therapeutic Use.

  • CAT Number: M005577
  • CAS Number: 471-74-9
  • Molecular Formula: C20H30O2
  • Molecular Weight: 302.458
  • Purity: ≥95%
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Related Small Molecules: 2-Acrylamidophenylboronic acid pinacol ester     1-Benzenesulfonate 1,2-Ethanediol     POLYETHYLENE-GRAFT-MALEIC ANHYDRIDE    

<span style="color:#000000;"><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;">Sandaracopimaric acid (CAS 471-74-9)&nbsp;<span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">is a natural product found in several plant species. It has a role as a plant metabolite. It was&nbsp;</span></span></span></span><span style="color:#000000;"><span style="caret-color: rgb(0, 0, 0); font-family: -webkit-standard; font-size: medium;"><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;">found to be an&nbsp;</span></span></span><span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;"><span style="caret-color: rgb(0, 0, 0);">lipoxygenase&nbsp;</span><span style="caret-color: rgb(0, 0, 0);">inhibitor.</span></span></span></span>


Catalog Number M005577
CAS Number 471-74-9
Synonyms

(1R)-1,2,3,4,4a,4bα,5,6,7,9,10,10aα-Dodecahydro-1,4aβ,7-trimethyl-7α-vinyl-1-phenanthrenecarboxylic acid;13-Methyl-17-norabieta-8(14),15-diene-18-oic acid

Molecular Formula C20H30O2
Purity ≥95%
Storage Room temperature
IUPAC Name (1R,4aR,4bS,7R,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
InChI InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18-,19+,20+/m0/s1
InChIKey MHVJRKBZMUDEEV-KRFUXDQASA-N
SMILES CC1(CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C)C=C
Reference

1: Afonso A. 4-carbomethoxy-5-alpha-androstane derivatives. Synthesis of (-)-sandaracopimaric acid. J Org Chem. 1970 Jun;35(6):1949-53. PubMed PMID: 5446989.<br />
2: Gao W, Dong X, Xie N, Zhou C, Fan Y, Chen G, Wang Y, Wei T, Zhu D. Dehydroabietic acid isolated from Commiphora opobalsamum causes endothelium-dependent relaxation of pulmonary artery via PI3K/Akt-eNOS signaling pathway. Molecules. 2014 Jun 23;19(6):8503-17. doi: 10.3390/molecules19068503. PubMed PMID: 24959678.<br />
3: Geisler K, Jensen NB, Yuen MM, Madilao L, Bohlmann J. Modularity of Conifer Diterpene Resin Acid Biosynthesis: P450 Enzymes of Different CYP720B Clades Use Alternative Substrates and Converge on the Same Products. Plant Physiol. 2016 May;171(1):152-64. doi: 10.1104/pp.16.00180. Epub 2016 Mar 2. PubMed PMID: 26936895; PubMed Central PMCID: PMC4854711.<br />
4: Zaugg J, Khom S, Eigenmann D, Baburin I, Hamburger M, Hering S. Identification and characterization of GABA(A) receptor modulatory diterpenes from Biota orientalis that decrease locomotor activity in mice. J Nat Prod. 2011 Aug 26;74(8):1764-72. doi: 10.1021/np200317p. Epub 2011 Jul 27. PubMed PMID: 21793559.<br />
5:<span style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">Comte, G., et al. &quot;Crystal structure of sandaracopimaric acid, a lipoxygenase inhibitor from Juniperus phoenicea.&quot;&nbsp;</span><i style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">Journal of Natural Products</i><span style="font-family: Arial, sans-serif; font-size: 13px; font-variant-ligatures: normal; orphans: 2; widows: 2;">&nbsp;58.2 (1995): 239-243.</span>

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