Juniperic acid

Juniperic acid or 16-hydroxyhexadecanoic acid is an omega-hydroxy long-chain fatty acid that is palmitic acid which is substituted at position 16 by a hydroxy group. Palmitic acid is converted to juniperic acid by cytochrome P450 various enzymes,[1] including CYP704B22.[2]

Juniperic acid
Names
IUPAC name
16-Hydroxyhexadecanoic acid
Other names
  • 16-Hydroxypalmitic acid
  • omega-Hydroxypalmitic acid
  • ω-Hydroxypalmitic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.299
EC Number
  • 208-028-7
KEGG
  • InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)
    Key: UGAGPNKCDRTDHP-UHFFFAOYSA-N
  • C(CCCCCCCC(=O)O)CCCCCCCO
Properties
C16H32O3
Molar mass 272.429 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

Juniperic acid is a key monomer of cutin in the plant cuticle.[3] It has a role as a plant metabolite.

References
  1. Van Bogaert, Inge N. A.; Groeneboer, Sara; Saerens, Karen; Soetaert, Wim (2011). "The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism". FEBS Journal. 278 (2): 206–221. doi:10.1111/j.1742-4658.2010.07949.x. PMID 21156025. S2CID 22920318.
  2. Li, Hui; Pinot, Franck; Sauveplane, Vincent; Werck-Reichhart, Danièle; Diehl, Patrik; Schreiber, Lukas; Franke, Rochus; Zhang, Ping; Chen, Liang; Gao, Yawei; Liang, Wanqi; Zhang, Dabing (2010). "Cytochrome P450 Family Member CYP704B2 Catalyzes the ω -Hydroxylation of Fatty Acids and is Required for Anther Cutin Biosynthesis and Pollen Exine Formation in Rice". The Plant Cell. 22 (1): 173–190. doi:10.1105/tpc.109.070326. PMC 2828706. PMID 20086189.
  3. "Metabocard for 16-Hydroxyhexadecanoic acid (HMDB0006294)". The Metabolomics Innovation Centre.
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