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Merck
CN

H8771

1-O-Palmityl-2-acetyl-sn-glycero-3-phospho-(N,N,N-trimethyl)hexanolamine

~95%

Synonym(s):

L-α-Phosphatidyl[N,N,N-trimethyl]hexanolamine, β-acetyl, γ-hexadecyl

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About This Item

Empirical Formula (Hill Notation):
C30H62NO7P
CAS Number:
99103-16-9
Molecular Weight:
579.79
UNSPSC Code:
12352211
PubChem Substance ID:
24895530
MDL number:
MFCD00077384

Key Documents

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InChI

1S/C32H67NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-24-27-37-29-32(40-31(2)34)30-39-41(35,36)38-28-25-22-20-23-26-33(3,4)5/h32H,6-30H2,1-5H3,(H,35,36)

SMILES string

CCCCCCCCCCCCCCCCCCOC[C@@H](COP(O)(=O)OCCCCCC[N](C)(C)C)OC(C)=O

InChI key

HRYXIYMPLGFZGG-UHFFFAOYSA-N

assay

~95%

form

solid

functional group

amine

shipped in

ambient

storage temp.

−20°C

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
071H01331

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A Tokumura et al.
The Journal of biological chemistry, 260(23), 12710-12714 (1985-10-15)
Several analogs of alkylacetylglycerophosphocholine (AGEPC; platelet-activating factor) were investigated as potential selective inhibitors of AGEPC-induced activation of washed rabbit platelets. Two particular compounds, CV-3988 (rac-3-(N-n-octadecylcarbamoyloxy)-2-methoxypropyl-2-thiazolioethyl++ + phosphate) and U66985 (1-O-octadecyl-2-acetyl-sn-glycero-3-phosphoric acid-6'-trimethylammonium-hexyl ester) emerged as particularly active and effective inhibitors. Aggregation
D B Buxton et al.
Biochemical pharmacology, 35(6), 893-897 (1986-03-15)
Stimulation of hepatic glycogenolysis and vasoconstriction of the hepatic vasculature in response to acetyl glyceryl ether phosphocholine (AGEPC; platelet activating factor) was inhibited by two structural analogues of AGEPC, U66985 (1-O-octadecyl-2-O-acetyl-sn-glycero-3-phosphoric acid-6'-trimethyl ammonium hexyl ester) and CV3988 [rac-3-(N-n-octadecylcarbamoyloxy)-2-methoxy-propyl-2-thiazolioethyl+ ++ phosphate].
J Sugatani et al.
Archives of biochemistry and biophysics, 246(2), 855-864 (1986-05-01)
1-O-Alkyl-2-acetyl-sn-glycero-3-phosphocholine (AGEPC) induced phosphorylation of two proteins having molecular masses of approximately 20- and 40-kDa in washed rabbit platelets in a concentration- and time-dependent manner. Sequential stimulation with AGEPC did not induce additional protein phosphorylation, supporting the concept of desensitization
C R Gandhi et al.
The Journal of biological chemistry, 265(30), 18234-18241 (1990-10-25)
Stimulation of rat Kupffer cells in primary culture with platelet-activating factor (PAF) caused a rapid hydrolysis of phosphatidylinositol 4,5-bisphosphate and phosphatidylinositol 4-phosphate with a concomitant increase in the levels of myo-inositol 1,4,5-trisphosphate and myo-inositol 1,4-bisphosphate. This phospholipase C-mediated hydrolysis of
H Homma et al.
Archives of biochemistry and biophysics, 252(1), 259-268 (1987-01-01)
Recently several synthetic analogs of 1-0-alkyl-2-acetyl-sn-glycero-3-phosphocholine (AGEPC; platelet-activating factor) were characterized as selective inhibitors of this agonist's effects on rabbit platelets (Tokumura, A., Homma, H., and Hanahan, D. J. (1985) J. Biol. Chem. 260, 12710-12714). In this current investigation, these
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