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Structure Database (LMSD)

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Common Name

Juniperic acid

Systematic Name

16-hydroxy-hexadecanoic acid

Synonyms

Juniperinic acid

LM ID

LMFA01050051

Formula

C₁₆H₃₂O₃

Exact Mass

Calculate m/z

272.235146

Sum Composition

FA 16:0;O

Status

Curated

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Classification

Biological Context

16-hydroxy Hexadecanoic acid is a metabolite of the saturated fatty acid palmitic acid (16:0) that has been hydroxylated on its terminal (ω) carbon. It is produced by ω-hydroxylation of palmitic acid by cytochrome P450 in both plants and animals.^1,2,3,4 In plants, it is commonly a component of cutin.^5,2

This information has been provided by Cayman Chemical

References

1. Aoyama, T., Hardwick, J.P., Imaoka, S., et al. Clofibrate-inducible rat hepatic P450s IVA1 and IVA3 catalyze the ω- and (ω-1)-hydroxylation of fatty acids and the (ω-1)-hydroxylation of prostaglandins E1 and F2α. J. Lipid Res. 31(8), 1477-1482 (1990).

2. Peshel, S., Franke, R., Schreiber, L., et al. Composition of the cuticle of developing sweet cherry fruit. Phytochemistry 68(7), 1017-1025 (2007).

3. Benveniste, I., Saito, T., Wang, Y., et al. Evolutionary relationship and substrate specificity of Arabidopsis thaliana fatty acid ω-hydroxylase. Plant Sci. 170(2), 326-328 (2006).

4. Roman, L.J., Palmer, C.N.A., Clark, J.E., et al. Expression of rabbit cytochromes P4504A which catalyze the ω-hydroxylation of arachidonic acid, fatty acid, and prostaglandins. Arch. Biochem. Biophys. 307(1), 57-65 (1993).

5. Li, H., Pinot, F., Sauveplane, V., et al. Cytochrome P450 family member CYP704B2 catalyzes the ω-hydroxylation of fatty acids and is require for anther cutin biosynthesis and pollen exine formation in rice. Plant Cell 22(1), 173-190 (2010).