An internal standard for the quantification of cis-6-hexadecenoic acid
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cis-6-Hexadecenoic Acid-d19

Item No. 28227

Technical Information
Formal Name
6Z-hexadecenoic-8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-d19 acid
CAS Number
2692623-89-3
Synonyms
  • C16:1(6Z)-d19
  • C16:1Δ6-d19
  • C16:1ω10c-d19
  • FA 16:1-d19
  • Sapienic Acid-d19
Molecular Formula
C16H11D19O2
Formula Weight
Purity
≥99% deuterated forms (d1-d19)
A 10 mg/ml solution in ethanol
Ethanol: Soluble
SMILES
[2H]C(C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])([2H])/C=C\CCCCC(O)=O
InChi Code
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10-/i1D3,2D2,3D2,4D2,5D2,6D2,7D2,8D2,9D2
InChi Key
NNNVXFKZMRGJPM-XZHWPFOISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    cis-6-Hexadecenoic acid-d19 is intended for use as an internal standard for the quantification of cis-6-hexadecenoic acid (Item No. 9001845) by GC- or LC-MS. cis-6-Hexadecenoic acid is a monounsaturated fatty acid and is one of the primary fatty acids in human skin.1 cis-6-Hexadecenoic acid levels are increased in isolated sebum from the face and back of patients with acne.2 In contrast, levels are decreased in the non-lesional skin and isolated sebum of atopic dermatitis patients, which correlates with an increase in S. aureus in the sebum.1 It is active against S. aureus in vitro when used at a concentration of 5 µg/ml at pH 5.5.3 cis-6-Hexadecenoic acid disrupts membrane integrity, the proton motive force, increases membrane fluidity, and inhibits the electron transport chain in S. aureus.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takigawa, H., Nakagawa, H., Kuzukawa, M., et alDeficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus. Dermatology 211(3), 240-248 (2005).

    2. Li, W.-H., Zhang, Q., Flach, C.R., et alIn vitro modeling of unsaturated free fatty acid-mediated tissue impairments seen in acne lesions. Arch. Dermatol. Res. 309(7), 529-540 (2017).

    3. Cartron, M.L., England, S.R., Chiriac, A.I., et alBactericidal activity of the human skin fatty acid cis-6-hexadecanoic acid on Staphylococcus aureus. Antimicrob. Agents Chemother. 58(7), 3599-3609 (2014).