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D1657

Sigma-Aldrich

1,3-Dioleoyl-2-palmitoylglycerol

≥99%

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Synonym(s):
1,3-Di(cis-9-octadecenoyl)-2-hexadecanoylglycerol
Empirical Formula (Hill Notation):
C55H102O6
CAS Number:
1716-07-0
Molecular Weight:
859.39
MDL number:
MFCD00057803
PubChem Substance ID:
24893508
NACRES:
NA.25

Quality Level

100

Assay

≥99%

form

liquid

functional group

ester

lipid type

neutral glycerides

shipped in

ambient

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCC\C=C\CCCCCCCC)COC(=O)CCCCCCC\C=C\CCCCCCCC

InChI

1S/C55H102O6/c1-4-7-10-13-16-19-22-25-27-30-32-35-38-41-44-47-53(56)59-50-52(61-55(58)49-46-43-40-37-34-29-24-21-18-15-12-9-6-3)51-60-54(57)48-45-42-39-36-33-31-28-26-23-20-17-14-11-8-5-2/h25-28,52H,4-24,29-51H2,1-3H3/b27-25+,28-26+

InChI key

PPTGNVIVNZLPPS-NBHCHVEOSA-N

Related Categories

General description

1,3-Dioleoyl-2-palmitoylglycerol (OPO) is a structured triglyceride in infant formula. Its structure is like human milk fat (HMF).

Application

1,3-Dioleoyl-2-palmitoylglycerol (OPO) has been used:
  • as a synthetic triacylglycerol (TAG) standard to investigate the fragmentation patterns of TAGs in milk fat by the multi-dimension mass spectrometry (MDMS) method
  • as a lipid standard to analyze OPO content/TAG compositions in the acidolysis products by high-performance liquid chromatography-evaporative light scattering detector (HPLC-ELSD)
  • as a standard in silver-ion HPLC separation of OPO-rich human milk fat substitute (HMFS)

Biochem/physiol Actions

1,3-Dioleoyl-2-palmitoylglycerol (OPO) exerts several beneficial effects on infants, including remitting constipation, improved calcium and fatty acid absorption, and improved bone development.

Packaging

Sealed ampule

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

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A Rosa et al.
Food & function, 7(9), 4092-4103 (2016-09-08)
We explored the changes in viability and lipid profile occurring in cancer cells, murine melanoma cells (B16F10 cells) and human cervical carcinoma cells (HeLa cells), when exposed to 24 h-treatments with an n-3 PUFA-rich oil obtained by supercritical extraction with
Fei Teng et al.
Food chemistry, 297, 124976-124976 (2019-06-30)
Milk fat is arguably one of the most complex fats found in nature and varies widely between animal species. Analysis of its digestion products is tremendously challenging, due to the complexity, diversity, and large range of concentrations of triacylglycerols (TAGs)
Jeung Hee Lee et al.
New biotechnology, 27(1), 38-45 (2009-11-03)
1,3-Dioleoyl-2-palmitoylglycerol (OPO)-rich human milk fat substitute (HMFS) was synthesized from tripalmitin-rich fraction and ethyl oleate by a lipase-catalyzed interesterification. Response surface methodology was employed to optimize its OPO content and acyl migration with reaction factors - substrate mole ratio of
Fei Teng et al.
Food chemistry, 297, 124976-124976 (2019-06-30)
Milk fat is arguably one of the most complex fats found in nature and varies widely between animal species. Analysis of its digestion products is tremendously challenging, due to the complexity, diversity, and large range of concentrations of triacylglycerols (TAGs)

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