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SML3331

Sigma-Aldrich

Triheptanoin

≥95% (HPLC)

Synonym(s):

Dermofeel TC 7, Glycerol trienanthate, Glyceryl triheptanoate, Heptanoic acid, 1,1′,1′′-(1,2,3-propanetriyl) ester, Heptanoic acid, 1,2,3-propanetriyl ester (9CI), Heptanoin, tri- (6CI,7CI,8CI), Lanol 37T, Trienanthoin, Triheptanoic glyceride, Trioenanthoin, UX007

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About This Item

Empirical Formula (Hill Notation):
C24H44O6
CAS Number:
620-67-7
Molecular Weight:
428.60
MDL number:
MFCD00042910
UNSPSC Code:
23201100
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

oil

color

colorless to brown

storage temp.

−20°C

SMILES string

O(C(COC(=O)CCCCCC)COC(=O)CCCCCC)C(=O)CCCCCC

InChI

1S/C24H44O6/c1-4-7-10-13-16-22(25)28-19-21(30-24(27)18-15-12-9-6-3)20-29-23(26)17-14-11-8-5-2/h21H,4-20H2,1-3H3

InChI key

PJHKBYALYHRYSK-UHFFFAOYSA-N

Biochem/physiol Actions

Triheptanoin is a triglyceride with 3 molar eq. of saturated heptanoic acid (C7:0). The even-chain FA does not occur naturally and is able to bypass metabolic block induced by enzyme deficiency and to replenish reduced tricarboxylic acid/TCA-cycle (Krebs cycle or citric acid cycle/CAC) intermediates (anaplerosis) in vivo.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

404.6 °F - open cup

Flash Point(C)

207 °C - open cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000178614
0000236261
0000240301
0000209601
0000257175

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Tesfaye W Tefera et al.
PloS one, 11(8), e0161816-e0161816 (2016-08-27)
There is increasing evidence that energy metabolism is disturbed in Amyotrophic Lateral Sclerosis (ALS) patients and animal models. Treatment with triheptanoin, the triglyceride of heptanoate, is a promising approach to provide alternative fuel to improve oxidative phosphorylation and aid ATP
Ingrid Sofia Vieira de Melo et al.
Nutricion hospitalaria, 32(1), 265-269 (2015-08-12)
the aim of this study was to evaluate the influence of consumption of a ketogenic diet supplemented with triheptanoin, a medium-chain anaplerotic triacylglycerol, on the liver fatty acid profile of Wistar rats. three groups of male Wistar rats (n =
Keri J Fogle et al.
Molecular genetics and metabolism, 126(4), 439-447 (2019-01-27)
Seizures are a feature not only of the many forms of epilepsy, but also of global metabolic diseases such as mitochondrial encephalomyopathy (ME) and glycolytic enzymopathy (GE). Modern anti-epileptic drugs (AEDs) are successful in many cases, but some patients are
T M Schwarzkopf et al.
Neuroscience, 300, 201-209 (2015-05-20)
Triheptanoin, an oily substance, consists of glycerol bound to three molecules of heptanoic acid, a C7 odd-chain fatty acid. A triheptanoin-rich diet has anaplerotic effects because heptanoate metabolism yields succinate which delivers substrates to the Krebs cycle. While previous studies
Tanya McDonald et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 40(3), 678-691 (2019-03-21)
Triheptanoin is anticonvulsant in several seizure models. Here, we investigated changes in glucose metabolism by triheptanoin interictally in the chronic stage of the pilocarpine mouse epilepsy model. After injection of [U-13C6]-glucose (i.p.), enrichments of 13C in intermediates of glycolysis and
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