Palmitic anhydride

Name: Palmitic anhydride
Brand: ALDRICH
Price: 59.5 USD
Availability: InStock

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/REAXYS Number:

1807507

EC Number:

210-805-0

MDL number:

MFCD00008992

UNSPSC Code:

12352100

PubChem Substance ID:

24857243

NACRES:

NA.22

Key Documents

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Quality Level

100

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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Show Differences

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This Item	358924	14353	P0500
Sigma-Aldrich 286508 Palmitic anhydride	Sigma-Aldrich 358924 (+)-O,O′-Diacetyl-L-tartaric anhydride	Sigma-Aldrich 14353 Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride	Sigma-Aldrich P0500 Palmitic acid
assay 97%	assay 97%	assay ≥95.0%	assay ≥99%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 200
mp 61-64 °C (lit.)	mp 130-135 °C (lit.)	mp -	mp 61-62.5 °C (lit.)
functional group anhydride	functional group anhydride, ester	functional group -	functional group carboxylic acid

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[1].

Application

Palmitic anhydride was used in the synthesis of water-soluble N-palmitoyl chitosan (PLCS) by coupling with swollen chitosan in dimethyl sulfoxide (DMSO)[2]. It was also used in the synthesis of N-acylphosphatidylserine[3].

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Purification and characterization of an N-acylphosphatidylserine from Rhodopseudomonas sphaeroides.

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.

Minimally oxidized LDL inhibits macrophage selective cholesteryl ester uptake and native LDL-induced foam cell formation.

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

Novel polymer micelles prepared from chitosan grafted hydrophobic palmitoyl groups for drug delivery.

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

Discovery of fatty acid ester metabolites of spirolide toxins in mussels from Norway using liquid chromatography/tandem mass spectrometry.

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

Assessment of acylation routes and structural characterisation by liquid chromatography/tandem mass spectrometry of semi-synthetic acyl ester analogues of lipophilic marine toxins.

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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Palmitic anhydride