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465-24-7-Longiborneol Longiborneol

Longiborneol

For research use only. Not for therapeutic Use.

  • CAT Number: I030974
  • CAS Number: 465-24-7
  • Molecular Formula: C15H26O
  • Molecular Weight: 222.372
  • Purity: 98%
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Related Small Molecules: Fibrinogen-Binding Peptide TFA     Pemafibrate     Thalidomide-5-NH2-C8-NH2 TFA    

Longiborneol is a sesquiterpene alcohol which has the same ring structure as culmorin.


Catalog Number I030974
CAS Number 465-24-7
Synonyms

Longiborneol

Molecular Formula C15H26O
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 1,4-Methanoazulen-9-ol, decahydro-1,5,5,8a-tetramethyl-, (1R,3aR,4S,8aS,9S)-
InChI InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)10-6-9-15(14,4)12(16)11(10)13/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+,14+,15+/m1/s1
InChIKey MNNFKQAYXGEKFA-MUGBGTHKSA-N
SMILES O[C@@H]1[C@]2(C)CC[C@]3([H])[C@@]1([H])C(C)(C)CCC[C@]23C
Reference

1: Schmidt R, Durling MB, de Jager V, Menezes RC, Nordkvist E, Svatoš A, Dubey M, Lauterbach L, Dickschat JS, Karlsson M, Garbeva P. Deciphering the genome and secondary metabolome of the plant pathogen Fusarium culmorum. FEMS Microbiol Ecol. 2018 Jun 1;94(6). doi: 10.1093/femsec/fiy078. PubMed PMID: 29718180.
2: Bresso E, Leroux V, Urban M, Hammond-Kosack KE, Maigret B, Martins NF. Structure-based virtual screening of hypothetical inhibitors of the enzyme longiborneol synthase-a potential target to reduce Fusarium head blight disease. J Mol Model. 2016 Jul;22(7):163. doi: 10.1007/s00894-016-3021-1. Epub 2016 Jun 21. PubMed PMID: 27324634.
3: Bahadoor A, Schneiderman D, Gemmill L, Bosnich W, Blackwell B, Melanson JE, McRae G, Harris LJ. Hydroxylation of Longiborneol by a Clm2-Encoded CYP450 Monooxygenase to Produce Culmorin in Fusarium graminearum. J Nat Prod. 2016 Jan 22;79(1):81-8. doi: 10.1021/acs.jnatprod.5b00676. Epub 2015 Dec 16. PubMed PMID: 26673640.
4: Sharma P, Shah GC. Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh, India. Nat Prod Res. 2015;29(9):883-6. doi: 10.1080/14786419.2014.990904. Epub 2014 Dec 17. PubMed PMID: 25515495.
5: Gaviria M, Quijano C, Pino J, Madriñán S. Chemical composition and antibacterial activity of the essential oil of Drimys granadensis L.f. leaves from Colombia. Chem Biodivers. 2011 Mar;8(3):532-9. doi: 10.1002/cbdv.201000170. PubMed PMID: 21404436.
6: McCormick SP, Alexander NJ, Harris LJ. CLM1 of Fusarium graminearum encodes a longiborneol synthase required for culmorin production. Appl Environ Microbiol. 2010 Jan;76(1):136-41. doi: 10.1128/AEM.02017-09. Epub 2009 Oct 30. PubMed PMID: 19880637; PubMed Central PMCID: PMC2798659.
7: Ihara M. Syntheses of biologically active natural products and leading compounds for new pharmaceuticals employing effective construction of a polycyclic skeleton. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):765-74. PubMed PMID: 16755041.
8: Takasu K. [Development of boomerang-type intramolecular cascade reactions and application to natural product synthesis]. Yakugaku Zasshi. 2001 Dec;121(12):887-98. Review. Japanese. PubMed PMID: 11766403.
9: Takasu K, Mizutani S, Noguchi M, Makita K, Ihara M. Total synthesis of (+/-)-culmorin and (+/-)-longiborneol: an efficient construction of Tricyclo[6.3.0.0(3,9)]undecan-10-one by intramolecular double Michael addition. J Org Chem. 2000 Jun 30;65(13):4112-9. PubMed PMID: 10866628.
10: Ihara M, Makita K, Fujiwara Y, Tokunaga Y, Fukumoto K. Stereoselective Construction of Copaborneol and Longiborneol Frameworks by Intramolecular Double Michael Reaction. J Org Chem. 1996 Sep 6;61(18):6416-6421. PubMed PMID: 11667485.

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