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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.)

functional group

acyl chloride

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

171158-5G:
171158-25G:
171158-VAR:
171158-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7996
MKCQ3123
MKCP5004
MKCN7567
MKCL4512

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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
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
A V Kabanov et al.
Biomedical science, 1(1), 63-67 (1990-01-01)
A method is proposed for the inhibition of viral reproduction in cells by means of fatty-acylated antiviral antibodies which, in contrast to the unmodified antibodies, have the ability to enter the cells. The potential of this technique is demonstrated in
[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
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