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Tripropionin

Tripropionin
Names
IUPAC name
2,3-di(propanoyloxy)propyl propanoate
Other names
Glycerol tripropionate; Glyceryl tripropionate; Glyceryl tripropanoate; Tripropionylglycerol; Tripropionine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.878 Edit this at Wikidata
EC Number
  • 205-365-1
UNII
  • InChI=1S/C12H20O6/c1-4-10(13)16-7-9(18-12(15)6-3)8-17-11(14)5-2/h9H,4-8H2,1-3H3
    Key: YZWRNSARCRTXDS-UHFFFAOYSA-N
  • CCC(=O)OCC(COC(=O)CC)OC(=O)CC
Properties
C12H20O6
Molar mass 260.286 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tripropionin, also known as glyceryl tripropionate, is a short-chain triglyceride (fat) composed of glycerol and three propionate (propionic acid) moieties.[1][2] It is a gradually converted precursor or prodrug of the short-chain fatty acid propionate and can be used to deliver this fatty acid.[1] Propionate itself is limited by an unpleasant smell and taste like vomit or body odor as well as rapid metabolism.[1] Tripropionin, via conversion into propionate, has been found to restore gut microbiota diversity, reduce colitis symptoms, improve gut barrier integrity, and produce anti-inflammatory effects in rodents.[1] There is interest in tripropionin, along with other short-chain triglycerides like tributyrin and triacetin, for potential use in dietary supplements and in treatment of gastrointestinal and other medical problems.[1][3][4] However, unlike other short-chain fatty acids, propionate has also been associated with various adverse effects, for instance neurotoxic effects, inflammation, increased anxiety and depression, and social impairment, with some such as anxiety and social deficits related to downregulation of the oxytocin receptor.[5][6]

See also

References

  1. ^ a b c d e Huang, Shouhe; He, Wensen; Yang, Haonan; Yan, Chi; Ding, Huafang; Chen, Zixing; Zhu, Hanyue; Hu, Kun; Chen, Zhen-Yu (2025). "Synthesis of tributyrin and tripropionin and their alleviative effects on colitis and gut microbiota in mice". Chemical Engineering Journal. 516 164178. Bibcode:2025ChEnJ.51664178H. doi:10.1016/j.cej.2025.164178. Retrieved 9 July 2026.
  2. ^ Howard J, Jackson MJ, Smyth DH (June 1970). "Intracellular hydrolysis of short chain glycerides by rat small intestine in vitro and transfer of glycerol". J Physiol. 208 (2): 461–471. doi:10.1113/jphysiol.1970.sp009131. PMC 1348760. PMID 5500736.
  3. ^ Duysburgh C, Verstrepen L, Van Meulebroek L, Marzorati M (2025). "Tributyrin (CoreBiome®) enhances butyrate levels and modulates the gut microbiota, barrier function, and immune response in vitro". Front Nutr. 12 1712993. doi:10.3389/fnut.2025.1712993. PMC 12746503. PMID 41473189.
  4. ^ Van den Abbeele P, Poppe J, Baudot A, Vu LD (September 2025). "Triacetin and a Mushroom Blend Restore Butyrate Production by IBS Microbiomes Ex Vivo, Thus Promoting Barrier Integrity". Int J Mol Sci. 26 (19): 9388. doi:10.3390/ijms26199388. PMC 12524982. PMID 41096656.
  5. ^ Prescott SL, Logan AC (2025). "Propionic Acid-Producing Bacteria as Provocateurs of Anxiety and Depression? [Letter]". Neuropsychiatr Dis Treat. 21: 257–258. doi:10.2147/NDT.S516386. PMC 11809391. PMID 39931199.
  6. ^ Huang L, Duan C, Xia X, Wang H, Wang Y, Zhong Z, Wang B, Ding W, Yang Y (January 2021). "Commensal microbe-derived propionic acid mediates juvenile social isolation-induced social deficits and anxiety-like behaviors". Brain Res Bull. 166: 161–171. doi:10.1016/j.brainresbull.2020.12.001. PMID 33279588. In addition, juvenile social isolation decreases the expression of oxytocin receptor (OXTR) in the medial prefrontal cortex (mPFC), and increases the amounts of fecal propionic acid (PA), a short-chain fatty acid derived from gut micobiota. Accordingly, infusion with an OXTR antagonist (OXTR-A, l-368,899) specifically in the mPFC or supplementation of PA both can cause social deficits and anxiety-like behaviors in group housed mice. [...] Intraventricular infusions of PA caused abnormal behavioral patterns, such as social deficits and anxiety-like behavior in rats similar to those seen in humans with ASD (Shultz et al., 2015, 2008; Thomas et al., 2012). Moreover, high levels of PA, but not other SCFAs, have been reported in the stools of ASD individuals (Wang et al., 2012). [...] We propose a model in which PA impairs social and emotional behavior by decreasing OXTR in the mPFC. Consistent with this model, we find that PA treatment decreases OXTR levels in the mPFC of GH mice (Fig. 6D, E) and causes social deficits and anxiety-like behaviors in GH mice (Fig. 6E-V). However, the precise mechanism by which PA decreases OXTR expression in the mPFC remains to be determined.
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