A lysophospholipid
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1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC

Item No. 37340

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,7R-dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphahentriaconta-13Z,16Z,19Z,22Z,25Z,28Z-hexaen-1-aminium, 4-oxide, inner salt
CAS Number
162440-05-3
Synonyms
  • 1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-Phosphocholine
  • LysoPC(22:6/0:0)
  • PC(22:6/0:0)
  • 22:6/0:0-PC
Molecular Formula
C30H50NO7P
Formula Weight
567.7
Purity
≥95% (as an 8:2 mixture of the 1-acyl and 2-acyl)
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/ml
SMILES
O[C@@H](COP([O-])(OCC[N+](C)(C)C)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O
InChi Code
InChI=1S/C30H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h6-7,9-10,12-13,15-16,18-19,21-22,29,32H,5,8,11,14,17,20,23-28H2,1-4H3/b7-6-,10-9-,13-12-,16-15-,19-18-,22-21-/t29-/m1/s1
InChi Key
LSOWKZULVQWMLY-APPDJCNMSA-N
Side Chain Carbon Sum
22:6
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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

    $41

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    5 mg

    $91

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    10 mg

    $159

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    25 mg

    $347

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    Product Description

    1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC is a lysophospholipid containing docosahexaenoic acid (DHA; Item Nos. 90310 | 17950) at the sn-1 position that has been found in shark liver extract.1 1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC decreases LPS-induced increases in TNF-α and IL-6 levels in RAW 264.7 cells in a concentration-dependent manner.2 It decreases LPS-induced production of nitric oxide (NO) in RAW 264.7 cells when used at concentrations ranging from 12 to 200 µM. 1-Docosahexaenoyl-2-hydroxy-sn-glycero-3-PC (15-500 µg/kg) inhibits plasma leakage into the peritoneum in a mouse model of peritonitis induced by zymosan A (Item No. 21175).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, S., and Li, K.W. Mass spectrometric identification of molecular species of phosphatidylcholine and lysophosphatidylcholine extracted from shark liver. J. Agric. Food Chem. 55(23), 9670-9677 (2007).

    2. Huang, L.S., Hung, N.D., Sok, D.-E., et al. Lysophosphatidylcholine containing docosahexaenoic acid at the sn-1 position is anti-inflammatory. Lipids 45(3), 225-236 (2010).