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MedKoo Cat#: 564531 | Name: Tormentic Acid
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Description:

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

Tormentic Acid is a natural anti-inflammatory agent which inhibits production of tumor necrosis factor‑α (TNF‑α), interleukin 6 (IL‑6), and IL‑1β. Tormentic Acid suppresses the NF-κB signaling pathway.

Chemical Structure

Tormentic Acid
CAS#13850-16-3

Theoretical Analysis

MedKoo Cat#: 564531

Name: Tormentic Acid

CAS#: 13850-16-3

Chemical Formula: C30H48O5

Exact Mass: 488.3502

Molecular Weight: 488.71

Elemental Analysis: C, 73.73; H, 9.90; O, 16.37

Price and Availability

Size Price Availability Quantity
1mg USD 275.00 2 Weeks
5mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Jacarandic acid, Tormentic Acid
IUPAC/Chemical Name
(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-Trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
InChi Key
OXVUXGFZHDKYLS-HIYYRCLUSA-N
InChi Code
InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21?,22-,23+,26-,27+,28?,29-,30+/m1/s1
SMILES Code
O=C([C@]12CC[C@@H](C)[C@@](C)(O)[C@@]1([H])C3=CCC4[C@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@]5([H])CCC4(C)[C@@]3(C)CC2)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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 488.71 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: Olech M, Ziemichód W, Nowacka-Jechalke N. The Occurrence and Biological Activity of Tormentic Acid-A Review. Molecules. 2021 Jun 22;26(13):3797. doi: 10.3390/molecules26133797. PMID: 34206442; PMCID: PMC8270333. 2: Wu J, Wang N, Jin G, Xue L. Tormentic acid induces anticancer effects in cisplatin-resistant human cervical cancer cells mediated via cell cycle arrest, ROS production, and targeting mTOR/PI3K/AKT signalling pathway. J BUON. 2020 Jan-Feb;25(1):74-79. PMID: 32277616. 3: Bay V, Gür S, Bayraktar O. Plant-derived tormentic acid alters the gut microbiota of the silkworm (Bombyx mori). Sci Rep. 2022 Jul 29;12(1):13005. doi: 10.1038/s41598-022-17478-4. PMID: 35906393; PMCID: PMC9338012. 4: Shi C, Li Z, Wu Y, Li X, Li Y, Wei J, Li J, Zhang Y, Li L. Euscaphic acid and Tormentic acid protect vascular endothelial cells against hypoxia-induced apoptosis via PI3K/AKT or ERK 1/2 signaling pathway. Life Sci. 2020 Jul 1;252:117666. doi: 10.1016/j.lfs.2020.117666. Epub 2020 Apr 13. PMID: 32298737. 5: Lin X, Li Y, Zhang X, Wei Y, Wen S, Lu Z, Huang Q, Wei J. Tormentic acid inhibits hepatic stellate cells activation via blocking PI3K/Akt/mTOR and NF-κB signalling pathways. Cell Biochem Funct. 2021 Jan;39(1):77-87. doi: 10.1002/cbf.3564. Epub 2020 Jun 21. Retraction in: Cell Biochem Funct. 2021 Oct;39(7):921. doi: 10.1002/cbf.3666. PMID: 32564421. 6: Lin X, Wei Y, Li Y, Xiong Y, Fang B, Li C, Huang Q, Huang R, Wei J. Tormentic Acid Ameliorates Hepatic Fibrosis in vivo by Inhibiting Glycerophospholipids Metabolism and PI3K/Akt/mTOR and NF-κB Pathways: Based on Transcriptomics and Metabolomics. Front Pharmacol. 2022 Mar 11;13:801982. doi: 10.3389/fphar.2022.801982. PMID: 35359829; PMCID: PMC8963336. 7: Bvumbi C, Chi GF, Stevens MY, Mombeshora M, Mukanganyama S. The Effects of Tormentic Acid and Extracts from Callistemon citrinus on Candida albicans and Candida tropicalis Growth and Inhibition of Ergosterol Biosynthesis in Candida albicans. ScientificWorldJournal. 2021 Sep 21;2021:8856147. doi: 10.1155/2021/8856147. PMID: 34594161; PMCID: PMC8478599. 8: He JY, Li J, Zhang YY, He HB, He YM, Xu DX, Wang X, Wu HY, Zhang JH, Jahid H, Sadia A, Yu HF, Wang JZ, Zou K. Tormentic acid, a triterpenoid isolated from the fruits of Chaenomeles speciose, protected indomethacin-induced gastric mucosal lesion via modulating miR-139 and the CXCR4/CXCL12/PLC/PKC/Rho a/MLC pathway. Pharm Biol. 2023 Dec;61(1):1343-1363. doi: 10.1080/13880209.2023.2249526. PMID: 37623313; PMCID: PMC10461523. 9: Wu J, Wang N, Jin G, Xue L. Tormentic acid induces anticancer effects in cisplatin-resistant human cervical cancer cells mediated via cell cycle arrest, ROS production, and targeting mTOR/PI3K/AKT signalling pathway. J BUON. 2021 Mar-Apr;26(2):643. PMID: 34077027. 10: Mashezha R, Mombeshora M, Mukanganyama S. Effects of Tormentic Acid and the Extracts from Callistemon citrinus on the Production of Extracellular Proteases by Staphylococcus aureus. Biochem Res Int. 2020 Apr 21;2020:6926320. doi: 10.1155/2020/6926320. PMID: 32399301; PMCID: PMC7211245. 11: Ma A, Wang Y, Zhang Q. Tormentic acid reduces inflammation in BV-2 microglia by activating the liver X receptor alpha. Neuroscience. 2015 Feb 26;287:9-14. doi: 10.1016/j.neuroscience.2014.12.005. Epub 2014 Dec 10. PMID: 25497374. 12: Ghosh C, Das MC, Acharjee S, Bhattacharjee S, Sandhu P, Kumari M, Bhowmik J, Ghosh R, Banerjee B, De UC, Akhter Y, Bhattacharjee S. Combating Staphylococcus aureus biofilm formation: the inhibitory potential of tormentic acid and 23-hydroxycorosolic acid. Arch Microbiol. 2023 Dec 18;206(1):25. doi: 10.1007/s00203-023-03762-y. PMID: 38108905. 13: Yue Y, Qiao B, Jiang X. Tormentic acid confers protection against oxidative stress injury in rats with Parkinson's disease by targeting the Wnt/β-catenin signaling pathway. Cell Mol Biol (Noisy-le-grand). 2020 Apr 20;66(1):32-36. PMID: 32359380. 14: Cui W, Sun C, Ma Y, Wang S, Wang X, Zhang Y. Neuroprotective effect of tormentic acid against memory impairment and neuro‑inflammation in an Alzheimer's disease mouse model. Mol Med Rep. 2020 Aug;22(2):739-750. doi: 10.3892/mmr.2020.11154. Epub 2020 May 18. PMID: 32468017; PMCID: PMC7339752. 15: Yang Y, Wang Y, Wang Y, Zhao M, Jia H, Li B, Xing D. Tormentic Acid Inhibits IL-1β-Induced Inflammatory Response in Human Osteoarthritic Chondrocytes. Inflammation. 2016 Jun;39(3):1151-9. doi: 10.1007/s10753-016-0349-8. PMID: 27102898. 16: Yang Y, Wang Y, Zhao M, Jia H, Li B, Xing D. Tormentic acid inhibits IL-1β-induced chondrocyte apoptosis by activating the PI3K/Akt signaling pathway. Mol Med Rep. 2018 Mar;17(3):4753-4758. doi: 10.3892/mmr.2018.8425. Epub 2018 Jan 12. PMID: 29328385. 17: Jian CX, Li MZ, Zheng WY, He Y, Ren Y, Wu ZM, Fan QS, Hu YH, Li CJ. Tormentic acid inhibits LPS-induced inflammatory response in human gingival fibroblasts via inhibition of TLR4-mediated NF-κB and MAPK signalling pathway. Arch Oral Biol. 2015 Sep;60(9):1327-32. doi: 10.1016/j.archoralbio.2015.05.005. Epub 2015 May 22. PMID: 26123747. 18: Kang HG, Lim JH, Kim HY, Kim H, Kim HM, Jeong HJ. Anti-fatigue effect of tormentic acid through alleviating oxidative stress and energy metabolism- modulating property in C2C12 cells and animal models. Nutr Res Pract. 2023 Aug;17(4):670-681. doi: 10.4162/nrp.2023.17.4.670. Epub 2023 Mar 3. PMID: 37529263; PMCID: PMC10375336. 19: Wu JB, Kuo YH, Lin CH, Ho HY, Shih CC. Tormentic acid, a major component of suspension cells of Eriobotrya japonica, suppresses high-fat diet-induced diabetes and hyperlipidemia by glucose transporter 4 and AMP-activated protein kinase phosphorylation. J Agric Food Chem. 2014 Nov 5;62(44):10717-26. doi: 10.1021/jf503334d. Epub 2014 Oct 27. PMID: 25317836. 20: Lin X, Zhang S, Huang R, Tan S, Liang S, Wu X, Zhuo L, Huang Q. Corrigendum to "Protective effect of tormentic acid from Potentilla chinensis against lipopolysaccharide/D-galactosamine induced fulminant hepatic failure in mice" [Int. Immunopharmacol. 19 (2014) 365-372]. Int Immunopharmacol. 2021 Jan;90:107244. doi: 10.1016/j.intimp.2020.107244. Epub 2020 Dec 11. Erratum for: Int Immunopharmacol. 2014 Apr;19(2):365-72. doi: 10.1016/j.intimp.2014.02.009. PMID: 33309532.

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