A component of lipid A
Related Products
Isomer(s)
451363(R)-hydroxy Palmitic Acid
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3-hydroxy Palmitic Acid

Item No. 19934

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-hydroxy-hexadecanoic acid
CAS Number
2398-34-7
Synonyms
  • FA 16:0;O
  • β-hydroxy Hexadecanoic Acid
  • β-hydroxy Palmitic Acid
  • DL-3-hydroxy Palmitic Acid
Molecular Formula
C16H32O3
Formula Weight
272.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.33 mg/mlEthanol: 2.5 mg/ml
SMILES
CCCCCCCCCCCCCC(O)CC(O)=O
InChi Code
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)
InChi Key
CBWALJHXHCJYTE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 mg

    $98

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    100 mg

    $157

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    250 mg

    $368

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    500 mg

    $637

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    Product Description

    3-hydroxy Palmitic acid is a form of the 16:0 lipid palmitic acid (Item No. 10006627). The lipid A part of lipopolysaccharides contain various 3-hydroxy fatty acids, making oxylipins such as 3-hydroxy palmitic acid useful as chemical markers of endotoxins.1 In R. solanacearum, 3-hydroxy palmitic acid is converted by an S-adenosyl methionine-dependent methyltransferase to 3-hydroxy palmitic acid methyl ester, which acts as a quorum sensing signal molecule for post-transcriptional modulation of genes involved in virulence.2 Long-chain 3-hydroxy fatty acids, such as 3-hydroxy palmitic acid, are also known to accumulate during long-chain 3-hydroxy-acyl-CoA dehydrogenase and mitochondrial trifunctional protein deficiencies.3 Such accumulation induces oxidative stress, leading to mitochondrial bioenergetics deregulation and eventual multi-organ dysfunction.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Uhlig, S., Negård, M., Heldal, K.K., et al. Profiling of 3-hydroxy fatty acids as environmental markers of endotoxin using liquid chromatography coupled to tandem mass spectrometry. J. Chromatogr. A 1434, 119-236 (2016).

    2. Shinohara, M., Nakajima, N., and Uehara, Y. Purification and characterization of a novel esterase (β-hydroxypalmitate methyl ester hydrolase) and prevention of the expression of virulence by Ralstonia solanacearum. J. Appl. Microbiol. 103(1), 152-162 (2007).

    3. Tonin, A.M., Amaral, A.U., Busanello, E.N., et al. Mitochondrial bioenergetics deregulation caused by long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies in rat brain: A possible role of mPTP opening as a pathomechanism in these disorders? Biochim. Biophys. Acta 1842(9), 1658-1667 (2014).