An acyl-CoA thioester
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Oleoyl-Coenzyme A (sodium salt)

Item No. 35384

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
coenzyme A, S-(9Z)-9-octadecenoate, monosodium salt
Synonyms
  • Oleoyl (cis-9-C18:1)-CoA
  • Oleoyl-CoA
Molecular Formula
C39H68N7O17P3S • Na
Formula Weight
1055.0
Purity
≥70%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: 10 mg/ml
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@H](COP(OP(OCC(C)(C)[C@@H](O)C(NCCC(NCCSC(CCCCCCC/C=C\CCCCCCCC)=O)=O)=O)(O)=O)(O)=O)[C@H]1OP(O)(O)=O.[Na]
InChi Code
InChI=1S/C39H68N7O17P3S.Na/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46;/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54);/b12-11-;/t28-,32-,33-,34+,38-;/m1./s1
InChi Key
FIGPJGJWOHHUEY-NMGRLVKYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $32

    Add

    5 mg

    $141

    Add

    10 mg

    $234

    Add

    25 mg

    $465

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Oleoyl-coenzyme A (oleoyl-CoA) is a thioester of oleic acid (Item No. 90260 | 24659) and CoA (Item Nos. 16147 | 21499 | 21722). It is a substrate for several acyl-CoA-dependent enzymes, including acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT-1), ACAT-2, acyl-CoA dehydrogenase-9 (ACAD-9), membrane-bound O-acyltransferase 1 (MBOAT1), and MBOAT2.1,2,3 Oleoyl-CoA binds the fatty acid metabolism regulator protein (FadR) promoter in E. coli (Ki = 0.005 µM).4 Oleoyl-CoA (1 µM) activates sulfonylurea receptor 1 (SUR1) linked to ATP-sensitive potassium channel Kir6.2 in Xenopus oocytes.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Seo, T., Oelkers, P.M., Giattina, M.R., et al. Differential modulation of ACAT1 and ACAT2 transcription and activity by long chain free fatty acids in cultured cells. Biochemistry 40(15), 4756-4762 (2001).

    2. Ensenauer, R., He, M., Willard, J.-M., et al. Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial β-oxidation of unsaturated fatty acids. The Journal of Biological Chemisty 280(37), 32309-32316 (2005).

    3. Gijón, M.A., Riekhof, W.R., Zarini, S., et al. Lysophospholipid acyltransferases and arachidonate recycling in human neutrophils. The Journal of Biological Chemisty 283(44), 30235-30245 (2008).

    4. DiRusso, C.C., Heimert, T.L., and Metzger, A.K. Characterization of FadR, a global transcriptional regulator of fatty acid metabolism in Escherichia coli. Interaction with the fadB promoter is prevented by long chain fatty acyl coenzyme A. The Journal of Biological Chemisty 267(12), 8685-8691 (1992).

    5. Gribble, F.M., Proks, P., Corkey, B.E., et al. Mechanism of cloned ATP-sensitive potassium channel activation by oleoyl-CoA. The Journal of Biological Chemisty 273(41), 26383-26387 (1998).