Juniperic acid

Juniperic acid

Names
IUPAC name 16-Hydroxyhexadecanoic acid
Other names 16-Hydroxypalmitic acid omega-Hydroxypalmitic acid ω-Hydroxypalmitic acid
Identifiers
CAS Number	506-13-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:55328
ChEMBL	ChEMBL4281719
ChemSpider	10034
ECHA InfoCard	100.007.299
EC Number	208-028-7
KEGG	C18218
PubChem CID	10466
CompTox Dashboard (EPA)	DTXSID6060133
InChI 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
SMILES C(CCCCCCCC(=O)O)CCCCCCCO
Properties
Chemical formula	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 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 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.