2D Structure
3D Structure
Properties | |
---|---|
PID | PID00088 |
Mol. Weight | 74.079 g/mol |
LogP | 0.48 |
Water solubility | 4.79 mol/L at 20 °C |
Hydrogen Bond Donor | 1 |
Hydrogen Bond Acceptor | 2 |
Rotatable Bonds | 1 |
XLogP3 | 0.3 |
Identifiers | |
---|---|
Formula | C3H6O2 |
PubChem CID | 1032 |
FEMA | 2924 |
Flavor Profile | Slightly Pungent Disagreeable, Rancid Odor, Sour & Mildly Cheese-Like; Fat, Fruit, Pungent, Silage, Soy |
Smiles | CCC(=O)O |
InChl Key | XBDQKXXYIPTUBI-UHFFFAOYSA-N |
InChl | InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5) |
CAS Registry Number | 79-09-4, 68937-68-8, 68990-37-4 |
IUPAC Systematic Name | None |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
---|---|---|---|---|---|
Great Burdock Fruit | Niu Bang Zi(牛蒡子) | Arctii Fructus | Cold, Bitter, Pungent | Bladder, Spleen, Liver,Stomach | View Graph |
Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
Propionic acid is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a clear liquid with a pungent and unpleasant smell, somewhat resembling body odor, short-chain fatty acid, fermentation product of the enteric microbiome,
naturally occurring carboxylic acid,clear liquid with a pungent and unpleasant smell, associated with human disorders involving mitochondrial dysfunction,
intermediate in cellular,can mimic/mediate the neurotoxic effects of autism,by-product of the human gut microbiome,impair cognition and sensorimotor ability in adult male rats,have neurotoxic
effect,have defect in the oxidation of propionic acid in vivo,Increasing Exercise Activity,promote rooting and fruiting, platform chemical in the food,
agriculture, and pharmaceutical industries,etc.
It can enhance the colonic barrier function.Continuous oral administration of propionic acid during lactation may increase its concentration in the
proximal colon and promote epithelial barrier function of proximal colon by enhancing the expression of ZO-1, Claudin-8, Claudin-1 and Occludin via
increases in the expression of ERK1/2 and p38 MAPK.Propionic acid inhibits the growth of mold and some bacteria at the levels between 0.1 and 1% by
weight,so most propionic acid produced is consumed as a preservative for both animal feed and food for human consumption.BODIPY FL propionic acid 1 is
a widely used fluorophore.Propionic acid is also useful as an intermediate in the production of other chemicals, especially polymers.In more specialized
applications, it is also used to make pesticides and pharmaceuticals.
Propionate acts as a metabolic toxin in liver cells by accumulating in mitochondria as propionyl-CoA and its derivative, methylcitrate, two tricarboxylic acid cycle inhibitors.When propionic acid is infused directly into rodents' brains, it produces reversible behavior (e.g., hyperactivity, dystonia, social impairment, perseveration) and brain changes. It also, being a three-carbon molecule, feeds into hepatic gluconeogenesis (that is, the creation of glucose molecules from simpler molecules in the liver).In a research ,propionic acid and carnitine treatment to hamsters caused an increase in adrenalin by 32% P <0.01).
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. Xia Z, Han Y, Wang K, Guo, S., Wu, D., Huang, X.,Zhu, L. Oral administration of propionic acid during lactation enhances the colonic barrier function[J]. Lipids in health and disease, 2017, 16(1): 62.
2. Katoh T, Yoshikawa M, Yamamoto T,Arai, R., Nii, N., Tomata, Y.,Yogo, T. Parallel fluorescent probe synthesis based on the large-scale preparation of BODIPY FL propionic acid[J]. Bioorganic & medicinal chemistry letters, 2017, 27(5): 1145-1148.
3. El-Ansary A, Shaker G, Siddiqi N J,Al-Ayadhi, L. Y. Possible ameliorative effects of antioxidants on propionic acid/clindamycin-induced neurotoxicity in Syrian hamsters[J]. Gut pathogens, 2013, 5(1): 32.
4. Goswami V, Srivastava A. Propionic acid production in an in situ cell retention bioreactor[J]. Applied microbiology and biotechnology, 2001, 56(5-6): 676-680.
5. Gallant M, Belley M, Carrire M C, Chateauneuf, A., Denis, D., Lachance, N., Truchon, J. F. StructureCactivity relationship of triaryl propionic acid analogues on the human EP3 prostanoid receptor[J]. Bioorganic & medicinal chemistry letters, 2003, 13(21): 3813-3816.
6. Staniek H, Krejpcio Z, Wieczorek D. The effects of high dietary doses of chromium (III) complex with propionic acid on nutritional and selected blood indices in healthy female rats[J]. Biological trace element research, 2016, 171(1): 192-200.
7. Guan N, Shin H, Chen R R,Li, J., Liu, L., Du, G., Chen, J. Understanding of how Propionibacterium acidipropionici respond to propionic acid stress at the level of proteomics[J]. Scientific reports, 2014, 4: 6951.
8. MacFabe D F, Cain D P, Rodriguez-Capote K, Franklin, A. E., Hoffman, J. E., Boon, F., Ossenkopp, K. P. Neurobiological effects of intraventricular propionic acid in rats: possible role of short chain fatty acids on the pathogenesis and characteristics of autism spectrum disorders[J]. Behavioural brain research, 2007, 176(1): 149-169.
9. Aschenbach J R, Kristensen N B, Donkin S S, Hammon, H. M., Penner, G. B. Gluconeogenesis in dairy cows: the secret of making sweet milk from sour dough[J]. IUBMB life, 2010, 62(12): 869-877.
10. https://en.wikipedia.org/wiki/Propionic_acid
11. https://www.youtube.com/watch?v=iDMuQtglPIw
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13.Aldbass A M, Bhat R S, El-Ansary A. Protective and therapeutic potency of N-acetyl-cysteine on propionic acid-induced biochemical autistic features in rats[J]. Journal of neuroinflammation, 2013, 10(1): 837.
14.Al-Ghamdi M, Al-Ayadhi L, El-Ansary A. Selected biomarkers as predictive tools in testing efficacy of melatonin and coenzyme Q on propionic acid-induced neurotoxicity in rodent model of autism[J]. BMC neuroscience, 2014, 15(1): 34
15.Kamen C L, Zevy D L, Ward J M, et al. Systemic Treatment with the Enteric Bacterial Fermentation Product, Propionic Acid, Reduces Acoustic Startle Response Magnitude in Rats in a Dose-Dependent Fashion: Contribution to a Rodent Model of ASD[J]. Neurotoxicity research, 2018: 1-7.
17.Lanzkowsky P. Manual of pediatric hematology and oncology[M]. Elsevier, 2005.
18.Alfawaz H, Al-Onazi M, Bukhari S I, et al. The Independent and Combined Effects of Omega-3 and Vitamin B12 in Ameliorating Propionic Acid Induced Biochemical Features in Juvenile Rats as Rodent Model of Autism[J]. Journal of Molecular Neuroscience, 2018, 66(3): 403-413
19.Ando T, Nyhan W L, Connor J D, et al. The oxidation of glycine and propionic acid in propionic acidemia with ketotic hyperglycinemia[J]. Pediatric research, 1972, 6(6): 576.
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