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L5753

Sigma-Aldrich

Linoleoyl chloride

≥99%, liquid

Synonym(s):

9,12-Octadecadienoyl chloride, (9Z,12Z)- (9CI, ACI)

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About This Item

Linear Formula:
C18H31OCl
CAS Number:
Molecular Weight:
298.89
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
Pricing and availability is not currently available.

biological source

plant

Assay

≥99%

form

liquid

density

0.93 g/mL at 25 °C (lit.)

functional group

chloro

lipid type

omega FAs

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O

InChI

1S/C18H31ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3/b7-6-,10-9-

InChI key

FBWMYSQUTZRHAT-HZJYTTRNSA-N

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Application

Linoleoyl chloride is used as a reagent for the synthesis of fatty acyl glyceric acids such as dilinoleoyl-D-glyceric acid

Packaging

Sealed ampule.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hiroshi Habe et al.
Journal of oleo science, 60(6), 327-331 (2011-05-25)
Previously, Lešová et al. reported the isolation and identification of metabolite OR-1, showing antitrypsin activity, produced during fermentation by Penicillium funiculosum. The structure of OR-1 was a mixture of glyceric acid (GA), esterified with C(14)-C(18) fatty acids, and oleic acid
Jing Xie et al.
BioMed research international, 2013, 710502-710502 (2013-07-19)
A novel antisense oligonucleotide (ASO) carrier, polyethylenimine conjugated to linoleic acid (PEI-LA), was synthesized and evaluated for delivery of LOR-2501 to tumor cells. LOR-2501 is an ASO targeting ribonucleotide reductase R1 subunit (RRM1). In this study, PEI-LA was synthesized by
Ahmed Abu-Fayyad et al.
International journal of pharmaceutics, 528(1-2), 463-470 (2017-06-20)
Gemcitabine is the first line therapy for pancreatic cancer. It is, however, extensively metabolized to the inactive form by deamination enzymatic reaction. Conjugation of gemcitabine with fatty acids on its 4-amino group was found to protect it from deamination deactivation
Shun Sato et al.
Journal of oleo science, 60(9), 483-487 (2011-08-20)
A novel derivative of glyceric acid (GA), dilinoleoyl-D-glyceric acid (LA₂-DGA), was synthesized from D-GA calcium salt and linoleoyl chloride and evaluated for cytotoxicity. The D-GA calcium salt was first reacted with 4-methoxybezylchloride, and the resulting compound was esterified with linoleoyl
Siddabasave Gowda B Gowda et al.
Antioxidants (Basel, Switzerland), 9(5) (2020-05-14)
Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are a recently discovered class of biologically active lipids with anti-inflammatory and anti-diabetic properties. Despite the possible link between endogenous FAHFA levels and nuclear factor erythroid 2-related factor 2 (Nrf2), their

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