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286508

Sigma-Aldrich

Palmitic anhydride

97%

Synonym(s):

Hexadecanoic anhydride

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About This Item

Linear Formula:
[CH3(CH2)14CO]2O
CAS Number:
623-65-4
Molecular Weight:
494.83
Beilstein:
1807507
EC Number:
210-805-0
MDL number:
MFCD00008992
UNSPSC Code:
12352100
PubChem Substance ID:
24857243
NACRES:
NA.22

Assay

97%

mp

61-64 °C (lit.)

functional group

anhydride
ester

SMILES string

CCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCC

InChI

1S/C32H62O3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31(33)35-32(34)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-30H2,1-2H3

InChI key

QWZBEFCPZJWDKC-UHFFFAOYSA-N

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General description

Palmitic anhydride reacted with 20-methyl spirolide G to form a derivative with a retention time and spectrum identical with the metabolite, 17-O-palmitoyl-20-methyl spirolide G.

Application

Palmitic anhydride was used in the synthesis of water-soluble N-palmitoyl chitosan (PLCS) by coupling with swollen chitosan in dimethyl sulfoxide (DMSO). It was also used in the synthesis of N-acylphosphatidylserine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV3081V
07418BF
05002DZ
00216DX

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John A B Aasen et al.
Rapid communications in mass spectrometry : RCM, 20(10), 1531-1537 (2006-04-22)
Cultured mussels sampled in the spring of 2002 and 2003 from Skjer, a location in the Sognefjord, Norway, tested positive in the mouse bioassay for lipophilic toxins. In a previous report, it was established that a number of spirolides, cyclic
Gang-Biao Jiang et al.
Molecular pharmaceutics, 3(2), 152-160 (2006-04-04)
Chitosan-based polymer micelles have a splendid outlook for drug delivery owing to the interesting properties, abundance, and low cost of chitosan. A new method of preparation of water-soluble N-palmitoyl chitosan (PLCS) which can form micelles in water is developed in
Jason M Meyer et al.
Journal of lipid research, 55(8), 1648-1656 (2014-06-04)
Scavenger receptor-mediated uptake of oxidized LDL (oxLDL) is thought to be the major mechanism of foam cell generation in atherosclerotic lesions. Recent data has indicated that native LDL is also capable of contributing to foam cell formation via low-affinity receptor-independent
T J Donohue et al.
Biochemistry, 21(11), 2765-2773 (1982-05-25)
A new phospholipid that can account for up to 40% of the total cellular phospholipid of Rhodopseudomonas sphaeroides has been identified. Purification of the phospholipid was accomplished by column chromatography on silicic acid and diethylaminoethylcellulose followed by preparative thin-layer chromatography.
Pablo de la Iglesia et al.
Rapid communications in mass spectrometry : RCM, 28(23), 2605-2616 (2014-11-05)
Esterification is one of the most important metabolic routes of lipophilic marine toxins in shellfish. In this work we assessed several chemical acylation reactions aimed at obtaining acyl ester analogues via partial synthesis from the free toxins. The procedures developed

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