A component of lipid A
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(R)-3-hydroxy Myristic Acid

Item No. 16871

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3R-hydroxy-tetradecanoic acid
CAS Number
28715-21-1
Synonyms
  • (R)-3-hydroxy Tetradecanoic Acid
  • FA 14:0;O
Molecular Formula
C14H28O3
Formula Weight
244.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 15 mg/ml
SMILES
CCCCCCCCCCC[C@@H](O)CC(O)=O
InChi Code
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
InChi Key
ATRNZOYKSNPPBF-CYBMUJFWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $108

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    25 mg

    $256

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    50 mg

    $322

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    100 mg

    $428

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    Product Description

    Lipopolysaccharides (LPS) are components of the cell walls of Gram-negative bacteria. LPS is composed of polysaccharides and lipid A, where lipid A is a phosphoglycolipid containing acyl chains composed of 10 to 16 carbons.1,2 The lipid A component of LPS is detected by Toll-like receptor 4 of mammalian leukocytes and, thus, is a key determinant in immune response.1 (R)-3-hydroxy Myristic acid is a form of the 14:0 lipid myristic acid (Item No. 13351) that is found in the lipid A component of some Gram-negative bacteria, including Escherichia, Haemophilus, Actinobacillus, and Campylobacter species.2,3 [Matreya, LLC. Catalog No. 1735]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Raetz, C.R., Reynolds, C.M., Trent, M.S., et al. Lipid A modification systems in Gram-negative bacteria. Annu. Rev. Biochem. 76, 295-329 (2007).

    2. Rietschel, E.T., Kirikae, T., Schade, F.U., et al. Bacterial endotoxin: Molecular relationships of structure to activity and function. FEBS J. 8(2), 217-225 (1994).

    3. Masoud, H., Weintraub, S.T., Wang, R., et al. Investigation of the structure of lipid A from Actinobacillus actinomycetemcomitans strain Y4 and human clinical isolate PO 1021-7. Eur. J. Biochem. 200(3), 775-781 (1991).