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MedKoo Cat#: 462930 | Name: Chebulic Acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chebulic acid is a phenol that has been found in T. chebular and has diverse biological activities. It reduces production of reactive oxygen species in human umbilical vein endothelial cells induced by glyceraldehyde-related advanced glycation end products when used at a concentration of 100 µg/ml. Chebulic acid reduces glycer-AGE-induced adhesion of HUVECs to THP-1 monocytes. It induces Nrf2 nuclear translocation and glutathione synthesis and inhibits glycer-AGE-induced collagen accumulation, a marker of fibrosis, in LX-2 hepatic stellate cells. In vivo, chebulic acid increases serum insulin levels and reduces blood urea nitrogen levels, proteinuria, albuminuria, and serum glucose levels in a diabetic rat model of ischemia-reperfusion-induced nephropathy.

Chemical Structure

Chebulic Acid
Chebulic Acid
CAS#23725-05-5

Theoretical Analysis

MedKoo Cat#: 462930

Name: Chebulic Acid

CAS#: 23725-05-5

Chemical Formula: C14H12O11

Exact Mass: 356.0380

Molecular Weight: 356.24

Elemental Analysis: C, 47.20; H, 3.40; O, 49.40

Price and Availability

Size Price Availability Quantity
5mg USD 650.00 2 Weeks
10mg USD 1,150.00 2 Weeks
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Related CAS #
No Data
Synonym
(–)-Chebulic Acid;
IUPAC/Chemical Name
(S)-2-((3S,4S)-3-carboxy-5,6,7-trihydroxy-1-oxoisochroman-4-yl)succinic acid
InChi Key
COZMWVAACFYLBI-XJEVXTIOSA-N
InChi Code
InChI=1S/C14H12O11/c15-5-1-4-7(10(19)9(5)18)8(3(12(20)21)2-6(16)17)11(13(22)23)25-14(4)24/h1,3,8,11,15,18-19H,2H2,(H,16,17)(H,20,21)(H,22,23)/t3-,8-,11-/m0/s1
SMILES Code
OC1=C(C(O)=CC2=C1[C@@]([H])([C@H](OC2=O)C(O)=O)[C@@H](C(O)=O)CC(O)=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 356.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yoo HJ, Hong CO, Ha SK, Lee KW. Chebulic Acid Prevents Methylglyoxal-Induced Mitochondrial Dysfunction in INS-1 Pancreatic β-Cells. Antioxidants (Basel). 2020 Aug 20;9(9):E771. doi: 10.3390/antiox9090771. PMID: 32825285. 2: Zhi MR, Gu XR, Han S, Liu KY, Liu ZQ, Tang YN, Han XT, Li F, Yang ZG, Tan P, Zhao HY, DU H. [Chemical variation in Aconti Kusnezoffii Radix before and after processing based on UPLC-Orbitrap-MS]. Zhongguo Zhong Yao Za Zhi. 2020 Mar;45(5):1082-1089. Chinese. doi: 10.19540/j.cnki.cjcmm.20191221.301. PMID: 32237450. 3: Yang ZN, Su BJ, Wang YQ, Liao HB, Chen ZF, Liang D. Isolation, Absolute Configuration, and Biological Activities of Chebulic Acid and Brevifolincarboxylic Acid Derivatives from Euphorbia hirta. J Nat Prod. 2020 Apr 24;83(4):985-995. doi: 10.1021/acs.jnatprod.9b00877. Epub 2020 Mar 6. PMID: 32141299. 4: Vora J, Athar M, Sinha S, Jha PC, Shrivastava N. Binding Insight of Anti-HIV Phytocompounds with Prime Targets of HIV: A Molecular Dynamics Simulation Analysis. Curr HIV Res. 2020;18(2):132-141. doi: 10.2174/1570162X18666200129112509. PMID: 31995010. 5: Cock IE, Rayan P. Ascorbic acid potentiates the Giardia duodenalis growth inhibitory activity of pure Terminalia ferdinandiana Exell compounds. Parasitol Res. 2020 Mar;119(3):1125-1137. doi: 10.1007/s00436-019-06579-1. Epub 2020 Jan 6. PMID: 31907666. 6: Zhang YL, Pan QM, Zhang GJ, Liang D. [Study on chemical constituents of stems and leaves of Sapium discolor]. Zhongguo Zhong Yao Za Zhi. 2019 Sep;44(17):3738-3744. Chinese. doi: 10.19540/j.cnki.cjcmm.20190614.201. PMID: 31602947. 7: Lee HR, Pyo MC, Chae SA, Hong CO, Lee KW. Inhibitory Effect of Chebulic Acid on Alveolar Epithelial to Mesenchymal Transition in Response to Urban Particulate Matter Using Co-treatment and Post-treatment Exposure. Biol Pharm Bull. 2019;42(8):1322-1331. doi: 10.1248/bpb.b19-00061. PMID: 31366867. 8: Vora J, Patel S, Athar M, Sinha S, Chhabria MT, Jha PC, Shrivastava N. Pharmacophore modeling, molecular docking and molecular dynamics simulation for screening and identifying anti-dengue phytocompounds. J Biomol Struct Dyn. 2020 Apr;38(6):1726-1740. doi: 10.1080/07391102.2019.1615002. Epub 2019 May 14. PMID: 31057055. 9: Jung HL, Yang SY, Pyo MC, Hong CO, Nam MH, Lee JW, Lee KW. Protective effects of chebulic acid from Terminalia chebula Retz. against t-BHP- induced oxidative stress by modulations of Nrf2 and its related enzymes in HepG2 cells. Food Sci Biotechnol. 2018 Sep 27;28(2):555-562. doi: 10.1007/s10068-018-0477-z. PMID: 30956868; PMCID: PMC6431318. 10: Vora J, Patel S, Sinha S, Sharma S, Srivastava A, Chhabria M, Shrivastava N. Molecular docking, QSAR and ADMET based mining of natural compounds against prime targets of HIV. J Biomol Struct Dyn. 2019 Jan;37(1):131-146. doi: 10.1080/07391102.2017.1420489. Epub 2018 Jan 7. PMID: 29268664. 11: Lee KW, Nam MH, Lee HR, Hong CO, Lee KW. Protective effects of chebulic acid on alveolar epithelial damage induced by urban particulate matter. BMC Complement Altern Med. 2017 Jul 19;17(1):373. doi: 10.1186/s12906-017-1870-5. PMID: 28724416; PMCID: PMC5518117. 12: Koo YC, Pyo MC, Nam MH, Hong CO, Yang SY, Lee KW. Chebulic acid prevents hepatic fibrosis induced by advanced glycation end-products in LX-2 cell by modulating Nrf2 translocation via ERK pathway. Toxicol In Vitro. 2016 Aug;34:8-15. doi: 10.1016/j.tiv.2016.03.013. Epub 2016 Mar 25. PMID: 27021876. 13: Gao J, Ajala OS, Wang CY, Xu HY, Yao JH, Zhang HP, Jukov A, Ma CM. Comparison of pharmacokinetic profiles of Terminalia phenolics after intragastric administration of the aqueous extracts of the fruit of Terminalia chebula and a Mongolian compound medicine-Gurigumu-7. J Ethnopharmacol. 2016 Jun 5;185:300-9. doi: 10.1016/j.jep.2016.03.016. Epub 2016 Mar 10. PMID: 26972503. 14: Olennikov DN, Kashchenko NI, Chirikova NK. In Vitro Bioaccessibility, Human Gut Microbiota Metabolites and Hepatoprotective Potential of Chebulic Ellagitannins: A Case of Padma Hepaten® Formulation. Nutrients. 2015 Oct 13;7(10):8456-77. doi: 10.3390/nu7105406. PMID: 26473917; PMCID: PMC4632426. 15: Ajala OS, Jukov A, Ma CM. Hepatitis C virus inhibitory hydrolysable tannins from the fruits of Terminalia chebula. Fitoterapia. 2014 Dec;99:117-23. doi: 10.1016/j.fitote.2014.09.014. Epub 2014 Sep 28. PMID: 25261266. 16: Lee JY, Oh JG, Kim JS, Lee KW. Effects of chebulic acid on advanced glycation endproducts-induced collagen cross-links. Biol Pharm Bull. 2014;37(7):1162-7. doi: 10.1248/bpb.b14-00034. Epub 2014 Apr 24. PMID: 24759763. 17: Pham AT, Malterud KE, Paulsen BS, Diallo D, Wangensteen H. α-Glucosidase inhibition, 15-lipoxygenase inhibition, and brine shrimp toxicity of extracts and isolated compounds from Terminalia macroptera leaves. Pharm Biol. 2014 Sep;52(9):1166-9. doi: 10.3109/13880209.2014.880486. Epub 2014 Mar 17. PMID: 24635511. 18: Pellati F, Bruni R, Righi D, Grandini A, Tognolini M, Pio Prencipe F, Poli F, Benvenuti S, Del Rio D, Rossi D. Metabolite profiling of polyphenols in a Terminalia chebula Retzius ayurvedic decoction and evaluation of its chemopreventive activity. J Ethnopharmacol. 2013 May 20;147(2):277-85. doi: 10.1016/j.jep.2013.02.025. Epub 2013 Mar 15. PMID: 23506992. 19: Silawat N, Gupta VB. Chebulic acid attenuates ischemia reperfusion induced biochemical alteration in diabetic rats. Pharm Biol. 2013 Jan;51(1):23-9. doi: 10.3109/13880209.2012.698288. Epub 2012 Sep 11. PMID: 22963650. 20: Kim JH, Hong CO, Koo YC, Kim SJ, Lee KW. Oral administration of ethyl acetate-soluble portion of Terminalia chebula conferring protection from streptozotocin-induced diabetic mellitus and its complications. Biol Pharm Bull. 2011;34(11):1702-9. doi: 10.1248/bpb.34.1702. PMID: 22040883.