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TRICAPRIN

Product NameTRICAPRIN
CAS621-71-6
MFC33H62O6
MW554.84
EINECS210-702-0
MOL File621-71-6.mol

Chemical Properties

Melting point	31-32 °C
Boiling point	254 °C / 5mmHg
Density	approximate 0.98 g/ml (20℃)
refractive index	approximate 1.44
Flash point	20 °C
storage temp.	-20°C
solubility	Chloroform (Sparingly), DMSO (Slightly, Sonicated)
form	Solid
color	White to Off-White
BRN	1717683
Cosmetics Ingredients Functions	SKIN CONDITIONING FRAGRANCE PERFUMING
InChI	1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3
InChIKey	LADGBHLMCUINGV-UHFFFAOYSA-N
SMILES	CCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
LogP	12.444 (est)
CAS DataBase Reference	621-71-6(CAS DataBase Reference)
EPA Substance Registry System	Glycerol tridecanoate (621-71-6)

Safety Information

Hazard Codes	F,Xn
Risk Statements	11-20/21/22
Safety Statements	26-28
RIDADR	UN 1282 3/PG 2
WGK Germany	-
RTECS	HE0100000
TSCA	TSCA listed
HS Code	29171900
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

1,2,3-Tridecanoyl glycerol is a triacylglycerol that contains decanoic acid at the sn-1, sn-2, and sn-3 positions. It has been found in human breast milk. 1,2,3-Tridecanoyl glycerol has been used as a standard for the quantification of triacylglycerols in fish oils by RP-HPLC. Formulations containing 1,2,3-tridecanoyl glycerol have been used in cosmetic products as thickening and skin-conditioning agents.

Uses

Tricaprin is used to construct solid lipid nanoparticles (SLNs) as delivery system for bromocriptine (B682600, Mesylate salt). It is also used in cationic SLNs to enhance p53 tumor suppressor gene transfer to lung cancer cells.

Definition

ChEBI: A triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by capric (decanoic) acid.

in vivo

Trisdecanoin (Intravenous injection (i.v.); 1h, 4h) can promote the metabolism of long chain fatty acids (LCFA) in the heart muscle of Atgl KO mice in lipotriglyceride lipase (Atgl) gene knockout (KO) mice. Effect of reducing lipid accumulation in the heart of AtglKO mice and improving left ventricular function of AtglKO mice^[2].
Trisdecanoin (1145 mg/kg/day; Oral gavage (p.o.); two weeks) can prevent and inhibit the development of abdominal aortic aneurysms and alleviate the apoptosis and dysfunction of early smooth muscle cells (SMCs) in Male Sprague-Dawley rat models^[3].

Animal Model:	Male Sprague-Dawley rats^[3]
Dosage:	1145 mg/kg/day
Administration:	Oral gavage (p.o.)
Result:	There was no significant difference in the incidence of AAA between the control and ricaprylin groups (30.2% vs 24.0%). In contrast, the incidence of AAA in Trisdecanoin was significantly lower than in the control group (30.2% vs. 3.6%). The AAA rupture rates in control group and C8-TG group were 31.3% and 33.3%, respectively. There was no aneurysm rupture in Trisdecanoin group. The mean aortic diameter of Trisdecanoin group was significantly lower than that of control group..

References

[1] KIM K M, PARK T S, SHIM S M. Optimization and validation of HRLC-MS method to identify and quantify triacylglycerol molecular species in human milk[J]. Analytical Methods, 2015, 10: 4362-4370. DOI: 10.1039/c5ay00591d
[2] áNGELA GARCíA SOLAESA. Characterization of triacylglycerol composition of fish oils by using chromatographic techniques.[J]. Journal of oleo science, 2014, 63 5: 449-460. DOI: 10.5650/jos.ess13202
[3] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.

TRICAPRIN

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