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M1890

Sigma-Aldrich

rac-Glycerol 1-myristate

≥99%

Synonym(s):

1-Monotetradecanoyl-rac-glycerol, rac-1-Myristoylglycerol, DL-α-Myristin, Monomyristin

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About This Item

Linear Formula:
H3C(CH2)12COOCH2CH(OH)CH2OH
CAS Number:
589-68-4
Molecular Weight:
302.45
Beilstein:
1727502
MDL number:
MFCD00046760
UNSPSC Code:
12352211
PubChem Substance ID:
24896704
NACRES:
NA.25

biological source

synthetic (organic)

Assay

≥99%

form

powder

functional group

ester
hydroxyl

lipid type

neutral glycerides

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCC(=O)OCC(O)CO

InChI

1S/C17H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)21-15-16(19)14-18/h16,18-19H,2-15H2,1H3

InChI key

DCBSHORRWZKAKO-UHFFFAOYSA-N

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General description

rac-Glycerol 1-myristate is present in the saw palmetto palm and is less soluble in water.

Application

rac-Glycerol 1-myristate has been used:
  • as a standard in liquid chromatography/atmospheric-pressure chemical ionization mass spectrometry (LC–APCI-MS) studies
  • as a representative monoacylglycerol to test its matrix effects in gas chromatography-mass spectrometry (GC-MS) studies
  • to test its antifungal activity against Fusarium spp.

Rac-glycerol 1-myristate (glycerol α-monomyristate) is used in colloidal chemistry as a nonionic surfactant in the development of micelles.

Biochem/physiol Actions

rac-Glycerol 1-myristate also elicits antifungal activity. It exhibits an anti-proliferative effect in HeLa cervical cancer cells when delivered as a polymeric nanoparticle-based conjugate.
rac-Glycerol 1-myristate, a 1-monoglyceride of myristic acid, has antibacterial activity against several Gram-positive bacterial strains.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hayami et al.
Journal of colloid and interface science, 220(2), 374-379 (1999-12-23)
The interfacial tension of a hexane solution of 1-monolaurin against water was measured as a function of temperature and concentration under atmospheric pressure. The thermodynamic quantity changes associated with the adsorption of 1-monolaurin were evaluated and compared with those of
Lok Kumar Shrestha et al.
The journal of physical chemistry. B, 113(18), 6290-6298 (2009-04-11)
In this paper we present the study of reverse micellar aggregates formed by glycerol alpha-monomyristate (C(14)G(1)) in different organic solvents. We have investigated the structure (mainly shape and size) of the monomyristin reverse micelles depending on alkyl chain length of
Wakako Tsuzuki
Lipids, 42(7), 613-619 (2007-06-22)
To elucidate the absorption characteristics of dietary lipids in the human intestine, we investigated the cellular uptake of lipid metabolites using a differential monolayer of the Caco2 cells. As lipid metabolites, several free fatty acids and 2-monoacylglycerols, were formed a
M Suman et al.
Journal of chromatography. A, 1216(18), 3758-3766 (2009-03-17)
A new, reliable liquid chromatography/atmospheric-pressure chemical ionisation mass spectrometry (LC-APCI-MS) method was developed for the quantitative determination of food emulsifiers composed of mono- and diacylglycerols of fatty acids (E471 series) in complex food matrices. These additives are extremely interesting for
Sirirat Boondireke et al.
Colloids and surfaces. B, Biointerfaces, 176, 9-17 (2018-12-28)
The cytotoxicity of monomyristin (MM), a monoacylglycerol, was investigated against cervical cancer cells (HeLa) and two normal cells (Vero and endometrial epithelial cells). MM exhibited cytotoxicity specifically to HeLa cells and not against normal cells except at the highest investigated
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