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171158

Sigma-Aldrich

Stearoyl chloride

97%

Synonym(s):

Octadecanoyl chloride

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About This Item

Linear Formula:
CH3(CH2)16COCl
CAS Number:
112-76-5
Molecular Weight:
302.92
Beilstein:
639784
EC Number:
204-004-5
MDL number:
MFCD00000744
UNSPSC Code:
12352100
eCl@ss:
39050509
PubChem Substance ID:
24850056
NACRES:
NA.22

Quality Level

200

Assay

97%

refractive index

n20/D 1.454 (lit.)

bp

174-178 °C/2 mmHg (lit.)

mp

21-22 °C (lit.)

density

0.897 g/mL at 25 °C (lit.)

SMILES string

CCCCCCCCCCCCCCCCCC(Cl)=O

InChI

1S/C18H35ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3

InChI key

WTBAHSZERDXKKZ-UHFFFAOYSA-N

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Application

Stearoyl chloride was used in the synthesis of 4-fluoroceramide. It was also used in the preparation of shimofuridin analogs: 2′-O-(4-O-stearoyl-alpha-L-fucopyranosyl)thymidine and -uridine.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jun Ning et al.
Carbohydrate research, 338(1), 55-60 (2002-12-31)
Two shimofuridin analogs: 2'-O-(4-O-stearoyl-alpha-L-fucopyranosyl)thymidine (2) and -uridine (3) have been synthesized using D-arabinose, L-fucose, thymine, uracil, and stearoyl chloride as the starting materials. The synthetic procedures involve the facile preparation of 1-(3,5-di-O-benzyl-beta-D-ribofuranosyl)thymine (9) and -uracil (10) by coupling of 1,2-anhydro-3,5-di-O-benzyl-alpha-D-ribofuranose
[Chemical modification of proteins (enzymes) by water-insoluble reagents].
A V Levashov et al.
Doklady Akademii nauk SSSR, 278(1), 246-248 (1984-09-01)
A M Ladhoff et al.
Biomedica biochimica acta, 43(7), 963-969 (1984-01-01)
The assembly of electron dense ferritin modified by acylation with steaorylchloride into small and large egg lecithin vesicles is reported. From electron micrographs conclusions are drawn: on the mode of ferritin incorporation in the lipid bilayer: Small liposomes seem to
Gergana S Nikolova et al.
Beilstein journal of organic chemistry, 4, 12-12 (2008-10-23)
Sphingolipids belong to the most important constituents of the membranes of eukaryotic cells. As intermediates in sphingolipid metabolism, sphingosine and its N-octadecanoyl-derivative, ceramide, exhibit a variety of biological functions. These compounds play a crucial role in many essential biological processes
R Koelsch et al.
Acta biologica et medica Germanica, 40(3), 331-335 (1981-01-01)
Enzymes, not anchored into bilayers of membranes like trypsin, alpha-chymotrypsin, and carboxypeptidase A are chemically modified by acylation with fatty acids chlorides. This treatment renders these proteins hydrophobic so that they can combine with the phospholipid membrane of liposomes. This
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