CHEBI:38403 - (R)-lamenallenic acid

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ChEBI Name (R)-lamenallenic acid
ChEBI ID CHEBI:38403
ChEBI ASCII Name (R)-lamenallenic acid
Definition The (R)-enantiomer of lamenallenic acid.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H30O2
Net Charge 0
Average Mass 278.436
Monoisotopic Mass 278.22458
InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-3,12,14H,4-11,15-17H2,1H3,(H,19,20)/b3-2+/t13-/m0/s1
InChIKey IHBRXZJPXHXMCN-IBUXWKBASA-N
SMILES C(CC=[C@]=C([H])CCCC(O)=O)CCCCCC\C=C\C
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R)-lamenallenic acid (CHEBI:38403) is a lamenallenic acid (CHEBI:38396)
(R)-lamenallenic acid (CHEBI:38403) is enantiomer of (S)-lamenallenic acid (CHEBI:38413)
Incoming (S)-lamenallenic acid (CHEBI:38413) is enantiomer of (R)-lamenallenic acid (CHEBI:38403)
IUPAC Name
(5R,16E)-octadeca-5,6,16-trienoic acid
Synonyms Sources
(−)-lamenallenic acid ChEBI
(−)-Lamenallensäure ChEBI
(−)-trans-5,6,16-octadecatrienoic acid ChEBI
(−)-trans-octadeca-5,6,16-trienoic acid ChEBI
(R,E)-5,6,16-octadecatrienoic acid ChEBI
(R,E)-octadeca-5,6,16-trienoic acid ChEBI
Registry Number Type Source
4136862 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16742552 PubMed citation Europe PMC
Last Modified
16 January 2020
General Comments
2007-06-05 The naturally occurring enantiomer isolated from Lamium purpureum seed oil. See: Mikolajczak, K.L., Rogers, M.F., Smith, C.R. and Wolff, I.A. (1967) An octadecatrienoic acid from Lamium purpureum L. seed oil containing 5,6-allenic and trans-16-olefinic unsaturation. Biochem. J. 105, 1245-1249. [PMID:16742552]
2007-06-05 See: Cowie, J.S., Landor, P.D., Landor, S.R. and Punja, N. (1972) Allenes. Part XXII. The synthesis and absolute configuration of laballenic and lamenallenic acids. J. Chem. Soc., Perkin Trans. 1, 2197-2201. [DOI:10.1039/P19720002197]