Draft:Tricaprin

Tricaprin
Names
	Preferred IUPAC name 2,3-di(decanoyloxy)propyl decanoate
	Other names Tridecanoin; Glyceryl tricaprate
Identifiers
CAS Number	621-71-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:77388;
ChemSpider	62521;
EC Number	210-702-0;
PubChem CID	69310;
UNII	O1PB8EU98M;
	InChI 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 Key: LADGBHLMCUINGV-UHFFFAOYSA-N;
	SMILES CCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC;
Properties
Chemical formula	C33H62O6
Molar mass	554.853 g·mol−1
Appearance	White (light yellow?) crystals
Melting point	31 °C (88 °F; 304 K)
Thermochemistry
Heat capacity (C)	1109 J/mol·K
Std enthalpy of; formation (ΔfH⦵298)	-1985.1 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	19861.4 ± 1.8 kJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Not classified as a hazardous substance
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>10 g/kg (mouse, intravenous)
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tracking categories (test):

SizeSet

Tricaprin or tridecanoin is a triglyceride of capric acid.^[4] Its formula is C₃₃H₆₂O₆.

Occurrence edit

Tricaprin occurs naturally in the seeds of Umbellularia californica, a hardwood tree native to North America.^[5]

Production edit

Uses edit

Tricaprin is used as an additive to diesel fuel^[6] and as part of current and speculative biodiesels.^[7]^[8]

Pharmacological edit

Tricaprin has been indicated as a possible drug to increase the production of insulin and decrease the production of androgen in the body when taken orally.^[9] It, along with other medium-chain triglycerides, has been studied as a treatment option to prevent ruptures of abdominal aortic aneurysm,^[10] and has been specifically studied as a regulator of membrane functions^[11] and in the heart to facilitate lipolysis.^[12]

References edit

^ ^a ^b "Tricaprin". Sigma-Aldrich. June 18, 2023.
^ ^a ^b ^c Decanoic acid, 1,2,3-propanetriyl ester in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
^ Wretlind A (October 1957). "The toxicity of low-molecular triglycerides". Acta Physiologica Scandinavica. 40 (4): 338–343. doi:10.1111/j.1748-1716.1957.tb01502.x. PMID 13478501.
^ Aimo L. "tricaprin (CHEBI:77388)". ChEBI. Retrieved April 12, 2024.
^ Reynolds T, Dring JV, Hughes C (December 1991). "Lauric acid-containing triglycerides in seeds of umbellularia californica nutt. (Lauraceae)". Journal of the American Oil Chemists' Society. 68 (12): 976–977. doi:10.1007/BF02657546. ISSN 0003-021X.
^ Eiteman MA, Goodrum JW (1993). "Rheology of the Triglycerides Tricaproin, Tricaprylin, and Tricaprin and of Diesel Fuel". Transactions of the ASAE. 36 (2): 503–507. doi:10.13031/2013.28366. ISSN 2151-0059.
^ Goodrum JW, Eiteman MA (April 1996). "Physical properties of low molecular weight triglycerides for the development of bio-diesel fuel models". Bioresource Technology. 56 (1): 55–60. doi:10.1016/0960-8524(95)00167-0.
^ Ferreira IM, de Ganzeli L, Rosset IG, Yoshioka SA, Porto AL (January 2017). "Ethylic Biodiesel Production Using Lipase Immobilized in Silk Fibroin-Alginate Spheres by Encapsulation". Catalysis Letters. 147 (1): 269–280. doi:10.1007/s10562-016-1917-0. ISSN 1011-372X.
^ "Tricaprin (Code C153424)". NCI Thesaurus. Retrieved April 12, 2024.
^ Kugo H, Sugiura Y, Fujishima R, Jo S, Mishima H, Sugamoto E, et al. (April 2023). "Tricaprin can prevent the development of AAA by attenuating aortic degeneration". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 160: 114299. doi:10.1016/j.biopha.2023.114299. PMID 36724640.
^ Ro SY, Choi HM, Choi SH, Lee SW, Lim SJ (July 2023). "Tricaprin as a membrane permeability regulator: sustained small hydrophilic substance release from liposomes". Journal of Pharmaceutical Investigation. 53 (4): 539–548. doi:10.1007/s40005-023-00621-2. ISSN 2093-5552.
^ Miyauchi H, Hirano KI, Nakano Y, Shimada K, Nishikawa M, Yamamoto H, et al. (2022). "¹²³I-BMIPP Scintigraphy Shows That CNT-01 (Tricaprin) Improves Myocardial Lipolysis in Patients with Idiopathic Triglyceride Deposit Cardiomyovasculopathy: First Randomized Controlled, Exploratory Trial for TGCV". Annals of Nuclear Cardiology. 8 (1): 67–75. doi:10.17996/anc.22-00167. PMC 9749752. PMID 36540180.

[sigmasds-1] "Tricaprin". Sigma-Aldrich. June 18, 2023.

[nist-2] Decanoic acid, 1,2,3-propanetriyl ester in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)

[3] Wretlind A (October 1957). "The toxicity of low-molecular triglycerides". Acta Physiologica Scandinavica. 40 (4): 338–343. doi:10.1111/j.1748-1716.1957.tb01502.x. PMID 13478501.

[4] Aimo L. "tricaprin (CHEBI:77388)". ChEBI. Retrieved April 12, 2024.

[5] Reynolds T, Dring JV, Hughes C (December 1991). "Lauric acid-containing triglycerides in seeds of umbellularia californica nutt. (Lauraceae)". Journal of the American Oil Chemists' Society. 68 (12): 976–977. doi:10.1007/BF02657546. ISSN 0003-021X.

[6] Eiteman MA, Goodrum JW (1993). "Rheology of the Triglycerides Tricaproin, Tricaprylin, and Tricaprin and of Diesel Fuel". Transactions of the ASAE. 36 (2): 503–507. doi:10.13031/2013.28366. ISSN 2151-0059.

[7] Goodrum JW, Eiteman MA (April 1996). "Physical properties of low molecular weight triglycerides for the development of bio-diesel fuel models". Bioresource Technology. 56 (1): 55–60. doi:10.1016/0960-8524(95)00167-0.

[8] Ferreira IM, de Ganzeli L, Rosset IG, Yoshioka SA, Porto AL (January 2017). "Ethylic Biodiesel Production Using Lipase Immobilized in Silk Fibroin-Alginate Spheres by Encapsulation". Catalysis Letters. 147 (1): 269–280. doi:10.1007/s10562-016-1917-0. ISSN 1011-372X.

[9] "Tricaprin (Code C153424)". NCI Thesaurus. Retrieved April 12, 2024.

[10] Kugo H, Sugiura Y, Fujishima R, Jo S, Mishima H, Sugamoto E, et al. (April 2023). "Tricaprin can prevent the development of AAA by attenuating aortic degeneration". Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie. 160: 114299. doi:10.1016/j.biopha.2023.114299. PMID 36724640.

[11] Ro SY, Choi HM, Choi SH, Lee SW, Lim SJ (July 2023). "Tricaprin as a membrane permeability regulator: sustained small hydrophilic substance release from liposomes". Journal of Pharmaceutical Investigation. 53 (4): 539–548. doi:10.1007/s40005-023-00621-2. ISSN 2093-5552.

[12] Miyauchi H, Hirano KI, Nakano Y, Shimada K, Nishikawa M, Yamamoto H, et al. (2022). "¹²³I-BMIPP Scintigraphy Shows That CNT-01 (Tricaprin) Improves Myocardial Lipolysis in Patients with Idiopathic Triglyceride Deposit Cardiomyovasculopathy: First Randomized Controlled, Exploratory Trial for TGCV". Annals of Nuclear Cardiology. 8 (1): 67–75. doi:10.17996/anc.22-00167. PMC 9749752. PMID 36540180.

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