Abscisic aldehyde

Abscisic aldehyde is an intermediate in the biosynthesis of the plant hormone abscisic acid.[1][2] It is produced by the dehydrogenation of xanthoxin by xanthoxin dehydrogenases, which is an NAD+ dependent short-chain dehydrogenase,[3] followed by selective oxidation by abscisic aldehyde oxygenase.[4]

Abscisic aldehyde
Names
Preferred IUPAC name
(2Z,4E)-5-[(1S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienal
Other names
Abscisyl aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C15H20O3/c1-11(6-8-16)5-7-15(18)12(2)9-13(17)10-14(15,3)4/h5-9, 18H,10H2,1-4H3/b7-5+,11-6-/t15-/m1/s1
    Key: RIKWDZWVHUIUAM-KICRZJJPSA-N
  • CC1=CC(=O)CC([C@]1(/C=C/C(=C\C=O)/C)O)(C)C
Properties
C15H20O3
Molar mass 248.322 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Ram K. Sindhu, David H. Griffin and Daniel C. Walton (1990). "Abscisic Aldehyde Is an Intermediate in the Enzymatic Conversion of Xanthoxin to Abscisic Acid in Phaseolus vulgaris L. Leaves". Plant Physiology. 93 (2): 689–694. doi:10.1104/pp.93.2.689. PMC 1062571. PMID 16667524.
  2. Seo, M; Koshiba, T (2002). "Complex regulation of ABA biosynthesis in plants". Trends in Plant Science. 7 (1): 41–8. doi:10.1016/S1360-1385(01)02187-2. PMID 11804826.
  3. Gonzalez-Guzman, M. (25 July 2002). "The Short-Chain Alcohol Dehydrogenase ABA2 Catalyzes the Conversion of Xanthoxin to Abscisic Aldehyde". The Plant Cell Online. 14 (8): 1833–1846. doi:10.1105/tpc.002477. PMC 151468. PMID 12172025.
  4. Seo, Mitsunori; Koiwai, Hanae; Akaba, Shuichi; Komano, Teruya; Oritani, Takayuki; Kamiya, Yuji; Koshiba, Tomokazu (August 2000). "Abscisic aldehyde oxidase in leaves of Arabidopsis thaliana". The Plant Journal. 23 (4): 481–488. doi:10.1046/j.1365-313x.2000.00812.x. PMID 10972874.


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