Acanthoic acid | CAS# 119290-87-8 | Anti-inflammatory agent

MedKoo Cat#: 571452 | Name: Acanthoic acid

Description:

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

Acanthoic acid is a pimaradiene diterpene isolated from Acanthopanax koreanum. It has been reported to have anti-inflammatory activities. Acanthoic acid downregulates LPS-induced TNF-α, IL-6 and IL-1β production in BALF, attenuates lung histopathologic changes, and inhibits inflammatory cytokines by stopping TNF-α, IL-6 and IL-1β production and NF-κB activation in LPS-stimulated alveolar macrophages.

Chemical Structure

Acanthoic acid

CAS#119290-87-8

Theoretical Analysis

MedKoo Cat#: 571452

Name: Acanthoic acid

CAS#: 119290-87-8

Chemical Formula: C20H30O2

Exact Mass: 302.2246

Molecular Weight: 302.46

Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Acanthoic acid; NP 1302: NP-1302; NP1302

IUPAC/Chemical Name

1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R-(1alpha,4aalpha,7alpha,8abeta,10abeta))-

InChi Key

TVHDZSRRHQKNEZ-MGFONVBGSA-N

InChi Code

InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,9,14,16H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14-,16-,18-,19-,20+/m0/s1

SMILES Code

O=C([C@]1(C)CCC[C@@]2(C)C3=CC[C@](C)(C=C)C[C@]3([H])CC[C@]12[H])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

>2 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 302.46 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.

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: Qiushi W, Guanghua L, Guangquan X. Acanthoic acid ameliorates lipopolysaccharide-induced acute lung injury. Eur J Pharmacol. 2015 Mar 5;750:32-8. doi: 10.1016/j.ejphar.2015.01.023. Epub 2015 Jan 23. PubMed PMID: 25620130. 2: Wei C, Tan CK, Xiaoping H, Junqiang J. Acanthoic acid inhibits LPS-induced inflammatory response in human gingival fibroblasts. Inflammation. 2015 Apr;38(2):896-901. doi: 10.1007/s10753-014-0051-7. PubMed PMID: 25373915. 3: Bai T, Yao YL, Jin XJ, Lian LH, Li Q, Yang N, Jin Q, Wu YL, Nan JX. Acanthoic acid, a diterpene in Acanthopanax koreanum, ameliorates the development of liver fibrosis via LXRs signals. Chem Biol Interact. 2014 Jul 25;218:63-70. doi: 10.1016/j.cbi.2014.04.016. Epub 2014 May 5. PubMed PMID: 24802811. 4: Través PG, Pimentel-Santillana M, Rico D, Rodriguez N, Miethke T, Castrillo A, Theodorakis EA, Martín-Sanz P, Palladino MA, Boscá L. Anti-inflammatory actions of acanthoic acid-related diterpenes involve activation of the PI3K p110γ/δ subunits and inhibition of NF-κB. Chem Biol. 2014 Aug 14;21(8):955-66. doi: 10.1016/j.chembiol.2014.06.005. Epub 2014 Jul 24. PubMed PMID: 25065531. 5: Suwancharoen S, Tommeurd W, Phurat C, Muangsin N, Pornpakakul S. Acanthoic Acid. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 5;66(Pt 7):o1531. doi: 10.1107/S1600536810019483. PubMed PMID: 21587780; PubMed Central PMCID: PMC3006772. 6: Yoon WJ, Ham YM, Yoon HS, Lee WJ, Lee NH, Hyun CG. Acanthoic acid inhibits melanogenesis through tyrosinase downregulation and melanogenic gene expression in B16 melanoma cells. Nat Prod Commun. 2013 Oct;8(10):1359-62. PubMed PMID: 24354173. 7: Wu YL, Jiang YZ, Jin XJ, Lian LH, Piao JY, Wan Y, Jin HR, Joon Lee J, Nan JX. Acanthoic acid, a diterpene in Acanthopanax koreanum, protects acetaminophen-induced hepatic toxicity in mice. Phytomedicine. 2010 May;17(6):475-9. doi: 10.1016/j.phymed.2009.07.011. PubMed PMID: 19836221. 8: Li Y, Zhang XS, Yu JL. Acanthoic acid inhibits LPS-induced inflammatory response by activating LXRα in human umbilical vein endothelial cells. Int Immunopharmacol. 2016 Mar;32:111-115. doi: 10.1016/j.intimp.2015.12.042. Epub 2016 Jan 22. PubMed PMID: 26803523. 9: Kim KN, Ham YM, Moon JY, Kim MJ, Jung YH, Jeon YJ, Lee NH, Kang N, Yang HM, Kim D, Hyun CG. Acanthoic acid induces cell apoptosis through activation of the p38 MAPK pathway in HL-60 human promyelocytic leukaemia. Food Chem. 2012 Dec 1;135(3):2112-7. doi: 10.1016/j.foodchem.2012.05.067. Epub 2012 May 23. PubMed PMID: 22953963. 10: Kang OH, Kim DK, Cai XF, Kim YH, Lee YM. Attenuation of experimental murine colitis by acanthoic acid from Acanthopanax koreanum. Arch Pharm Res. 2010 Jan;33(1):87-93. doi: 10.1007/s12272-010-2230-x. Epub 2010 Feb 27. PubMed PMID: 20191349. 11: Traves PG, Hortelano S, Zeini M, Chao TH, Lam T, Neuteboom ST, Theodorakis EA, Palladino MA, Castrillo A, Bosca L. Selective activation of liver X receptors by acanthoic acid-related diterpenes. Mol Pharmacol. 2007 Jun;71(6):1545-53. Epub 2007 Feb 28. PubMed PMID: 17329499. 12: Ling T, Chowdhury C, Kramer BA, Vong BG, Palladino MA, Theodorakis EA. Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid. J Org Chem. 2001 Dec 28;66(26):8843-53. PubMed PMID: 11749614. 13: Kim JA, Kim DK, Jin Tae, Kang OH, Choi YA, Choi SC, Kim TH, Nah YH, Choi SJ, Kim YH, Bae KH, Lee YM. Acanthoic acid inhibits IL-8 production via MAPKs and NF-kappaB in a TNF-alpha-stimulated human intestinal epithelial cell line. Clin Chim Acta. 2004 Apr;342(1-2):193-202. PubMed PMID: 15026281. 14: Nan JX, Jin XJ, Lian LH, Cai XF, Jiang YZ, Jin HR, Lee JJ. A diterpenoid acanthoic acid from Acanthopanax koreanum protects against D-galactosamine/lipopolysaccharide-induced fulminant hepatic failure in mice. Biol Pharm Bull. 2008 Apr;31(4):738-42. PubMed PMID: 18379074. 15: Lee KO, Min KH, Suh YG. Synthesis of C4-modified acanthoic acid analogs and their biological evaluation as nitric oxide inhibitors. Arch Pharm Res. 2005 Jun;28(6):648-51. PubMed PMID: 16042071. 16: Kok BP, Saez E. Activating PI3-kinase to dampen inflammation. Chem Biol. 2014 Aug 14;21(8):917-8. doi: 10.1016/j.chembiol.2014.07.012. PubMed PMID: 25126986; PubMed Central PMCID: PMC4135385. 17: Kang HS, Song HK, Lee JJ, Pyun KH, Choi I. Effects of acanthoic acid on TNF-alpha gene expression and haptoglobin synthesis. Mediators Inflamm. 1998;7(4):257-9. PubMed PMID: 9792335; PubMed Central PMCID: PMC1781859. 18: Jung HJ, Shim JS, Suh YG, Kim YM, Ono M, Kwon HJ. Potent inhibition of in vivo angiogenesis and tumor growth by a novel cyclooxygenase-2 inhibitor, enoic acanthoic acid. Cancer Sci. 2007 Dec;98(12):1943-8. Epub 2007 Sep 19. PubMed PMID: 17888030. 19: Kang OH, Choi YA, Park HJ, Kang CS, Song BS, Choi SC, Nah YH, Yun KJ, Cai XF, Kim YH, Bae KH, Lee YM. Inhibition of trypsin-induced mast cell activation by acanthoic acid. J Ethnopharmacol. 2006 May 24;105(3):326-31. Epub 2006 Jan 18. PubMed PMID: 16414226. 20: Kang HS, Kim YH, Lee CS, Lee JJ, Choi I, Pyun KH. Suppression of interleukin-1 and tumor necrosis factor-alpha production by acanthoic acid, (-)-pimara-9(11),15-dien-19-oic acid, and it antifibrotic effects in vivo. Cell Immunol. 1996 Jun 15;170(2):212-21. PubMed PMID: 8660820.