Fraxinellone | CAS#28808-62-0

MedKoo Cat#: 525140 | Name: Fraxinellone

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Description:

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

Fraxinellone has anti-inflammatory properties. Fraxinellone was found to inhibit LPS-induced nitric oxide (NO) and prostaglandin E(2) (PGE(2)) production, and to reduce the LPS-induced expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the mRNA and protein levels in a dose-dependent manner.

Chemical Structure

Fraxinellone

CAS#28808-62-0

Theoretical Analysis

MedKoo Cat#: 525140

Name: Fraxinellone

CAS#: 28808-62-0

Chemical Formula: C14H16O3

Exact Mass: 232.1099

Molecular Weight: 232.28

Elemental Analysis: C, 72.39; H, 6.94; O, 20.66

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 450.00	2 Weeks
250mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Fraxinellone; NSC638730; NSC 638730; NSC-638730

IUPAC/Chemical Name

(3R,3aR)-3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one

InChi Key

XYYAFLHHHZVPRN-JSGCOSHPSA-N

InChi Code

InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14-/m0/s1

SMILES Code

C1(C=2[C@@]([C@@H](O1)c1cocc1)(CCCC2C)C)=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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Fraxinellone is a PD-L1 inhibitor and inhibits HIF-1α protein synthesis without affecting HIF-1α protein degradation.

In vitro activity:

Lipopolysaccharide stimulation significantly upregulated the levels of inflammatory factors, which were inhibited by fraxinellone intervention. Moreover, fraxinellone notably promoted osteogenic differentiation and calcification shown by increasing levels of alkaline phosphatase, calcification and osteogenic marker proteins. Furthermore, the expression of BMP2, phosphorylated Smad1 and phosphorylated Smad5 was remarkably upregulated when fraxinellone exposure in lipopolysaccharide-induced PDLSCs. Reference: Arch Oral Biol. 2021 Jan;121:104927. https://pubmed.ncbi.nlm.nih.gov/33137544/

In vivo activity:

The present study showed that fraxinellone could alleviate folic acid-induced kidney fibrosis in mice in a dose dependent manner. Reference: Toxicol Appl Pharmacol. 2021 Jun 1;420:115530. https://pubmed.ncbi.nlm.nih.gov/33845055/

	Solvent	mg/mL	mM
Solubility
	DMSO	73.0	314.28

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 232.28 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

Formulation protocol:

1. Fu Z, Wang X, Li B, Tang Y. Fraxinellone alleviates inflammation and promotes osteogenic differentiation in lipopolysaccharide-stimulated periodontal ligament stem cells by regulating the bone morphogenetic protein 2/Smad pathway. Arch Oral Biol. 2021 Jan;121:104927. doi: 10.1016/j.archoralbio.2020.104927. Epub 2020 Oct 7. PMID: 33137544. 2. Kim MJ, Bae GS, Jo IJ, Choi SB, Kim DG, Jung HJ, Song HJ, Park SJ. Fraxinellone inhibits inflammatory cell infiltration during acute pancreatitis by suppressing inflammasome activation. Int Immunopharmacol. 2019 Apr;69:169-177. doi: 10.1016/j.intimp.2019.01.043. Epub 2019 Feb 1. PMID: 30716587. 3. He B, Zhang W, He J. Fraxinellone Has Anticancer Activity by Inducing Osteosarcoma Cell Apoptosis via Promoting Excessive Autophagy Flux. Front Pharmacol. 2021 Apr 19;12:653212. doi: 10.3389/fphar.2021.653212. PMID: 33953684; PMCID: PMC8090933. 4. Zheng B, Yuan M, Wang S, Tan Y, Xu Y, Ye J, Gao Y, Sun X, Wang T, Kong L, Wu X, Xu Q. Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation. Toxicol Appl Pharmacol. 2021 Jun 1;420:115530. doi: 10.1016/j.taap.2021.115530. Epub 2021 Apr 13. PMID: 33845055.

In vitro protocol:

In vivo protocol:

1. He B, Zhang W, He J. Fraxinellone Has Anticancer Activity by Inducing Osteosarcoma Cell Apoptosis via Promoting Excessive Autophagy Flux. Front Pharmacol. 2021 Apr 19;12:653212. doi: 10.3389/fphar.2021.653212. PMID: 33953684; PMCID: PMC8090933. 2. Zheng B, Yuan M, Wang S, Tan Y, Xu Y, Ye J, Gao Y, Sun X, Wang T, Kong L, Wu X, Xu Q. Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation. Toxicol Appl Pharmacol. 2021 Jun 1;420:115530. doi: 10.1016/j.taap.2021.115530. Epub 2021 Apr 13. PMID: 33845055.

1: Li Q, Huang X, Li S, Ma J, Lv M, Xu H. Semisynthesis of Esters of Fraxinellone C4/10-Oxime and Their Pesticidal Activities. J Agric Food Chem. 2016 Jul 5. [Epub ahead of print] PubMed PMID: 27338830. 2: Wu XF, Ouyang ZJ, Feng LL, Chen G, Guo WJ, Shen Y, Wu XD, Sun Y, Xu Q. Suppression of NF-κB signaling and NLRP3 inflammasome activation in macrophages is responsible for the amelioration of experimental murine colitis by the natural compound fraxinellone. Toxicol Appl Pharmacol. 2014 Nov 15;281(1):146-56. doi: 10.1016/j.taap.2014.10.002. Epub 2014 Oct 13. PubMed PMID: 25448682. 3: Lv M, Wu W, Liu H. Effects of Fraxinellone on the midgut enzyme activities of the 5th Instar Larvae of Oriental Armyworm, Mythimna separata walker. Toxins (Basel). 2014 Sep 11;6(9):2708-18. doi: 10.3390/toxins6092708. PubMed PMID: 25216084; PubMed Central PMCID: PMC4179156. 4: Guo Y, Qu H, Zhi X, Yu X, Yang C, Xu H. Semisynthesis and insecticidal activity of some fraxinellone derivatives modified in the B ring. J Agric Food Chem. 2013 Dec 11;61(49):11937-44. doi: 10.1021/jf404195m. Epub 2013 Nov 25. PubMed PMID: 24261313. 5: Wang P, Sun J, Gao E, Zhao Y, Qu W, Yu Z. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jun 1;928:44-51. doi: 10.1016/j.jchromb.2013.03.018. Epub 2013 Mar 26. PubMed PMID: 23611843. 6: Lü M, Wu W, Liu H. Insecticidal and feeding deterrent effects of fraxinellone from Dictamnus dasycarpus against four major pests. Molecules. 2013 Mar 1;18(3):2754-62. doi: 10.3390/molecules18032754. PubMed PMID: 23455666. 7: Guo Y, Yan YY, Yang C, Yu X, Zhi XY, Xu H. Regioselective synthesis of fraxinellone-based hydrazone derivatives as insecticidal agents. Bioorg Med Chem Lett. 2012 Sep 1;22(17):5384-7. doi: 10.1016/j.bmcl.2012.07.058. Epub 2012 Jul 21. PubMed PMID: 22858136. 8: Guo Y, Yan Y, Yu X, Wang Y, Zhi XY, Hu Y, Xu H. Synthesis and insecticidal activity of some novel fraxinellone-based esters. J Agric Food Chem. 2012 Jul 18;60(28):7016-21. doi: 10.1021/jf301734h. Epub 2012 Jul 2. PubMed PMID: 22724658. 9: Gu HM, Xu H, Zhong ZZ, Zhu HL, Li QS. Fraxinellone. Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):o1472. doi: 10.1107/S1600536811018393. Epub 2011 May 20. PubMed PMID: 21754842; PubMed Central PMCID: PMC3120588. 10: Wang S, Zhu W, Ou S, Guan Y, Chen L, Yang M. [Effects of penetration enhancers on in vitro percutaneous absorption and amount retained in skin of paeonol, dictamnine, fraxinellone and glycyrrhetinic acid in Liangfu cream]. Zhongguo Zhong Yao Za Zhi. 2009 Jul;34(14):1778-82. Chinese. PubMed PMID: 19894505. 11: Lee CS, Won C, Yoo H, Yi EH, Cho Y, Maeng JW, Sung SH, Ye SK, Chung MH. Inhibition of double-stranded RNA-induced inducible nitric oxide synthase expression by fraxinellone and sauchinone in murine microglia. Biol Pharm Bull. 2009 Nov;32(11):1870-4. PubMed PMID: 19881300. 12: Kim JH, Park YM, Shin JS, Park SJ, Choi JH, Jung HJ, Park HJ, Lee KT. Fraxinellone inhibits lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by negatively regulating nuclear factor-kappa B in RAW 264.7 macrophages cells. Biol Pharm Bull. 2009 Jun;32(6):1062-8. PubMed PMID: 19483316. 13: Sun Y, Qin Y, Gong FY, Wu XF, Hua ZC, Chen T, Xu Q. Selective triggering of apoptosis of concanavalin A-activated T cells by fraxinellone for the treatment of T-cell-dependent hepatitis in mice. Biochem Pharmacol. 2009 Jun 1;77(11):1717-24. doi: 10.1016/j.bcp.2009.03.002. Epub 2009 Mar 14. PubMed PMID: 19428326. 14: Ran QQ, Ruan LP, Zhu DN, Yu BY. [Improving the solubility of fraxinellone to increase its oral bioavailability and hepatoprotective action against acute liver injury in mice]. Yao Xue Xue Bao. 2007 Jun;42(6):675-80. Chinese. PubMed PMID: 17702408. 15: Yuan CL, Yang DS. [Determination of fraxinellone in root bark of Dictamnus dasycarpus by RP-HPLC]. Zhongguo Zhong Yao Za Zhi. 2006 Jun;31(12):992-4. Chinese. PubMed PMID: 17048647. 16: Yang RL, Jia TL, Zhang RQ. Microbial transformation of fraxinellone by Aspergillus niger. J Asian Nat Prod Res. 2005 Dec;7(6):843-5. PubMed PMID: 16308202. 17: Trudeau S, Morken JP. Short and efficient total synthesis of fraxinellone limonoids using the stereoselective Oshima-Utimoto reaction. Org Lett. 2005 Nov 24;7(24):5465-8. PubMed PMID: 16288532. 18: Yu SM, Ko FN, Su MJ, Wu TS, Wang ML, Huang TF, Teng CM. Vasorelaxing effect in rat thoracic aorta caused by fraxinellone and dictamine isolated from the Chinese herb Dictamnus dasycarpus Turcz: comparison with cromakalim and Ca2+ channel blockers. Naunyn Schmiedebergs Arch Pharmacol. 1992 Mar;345(3):349-55. PubMed PMID: 1377790.