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

Hodoodo CAT#: H540227

CAS#: 482-45-1

Description: Isoimperatorin is a COX-2 inhibitor. It induces cell cycle arrest and inhibits proliferation in melanoma cells, prevents activation of carcinogens, increases expression of PPAR-γ, and suppresses degranulation of bone marrow-derived mast cells.

Chemical Structure

Isoimperatorin

CAS# 482-45-1

Instruction

Theoretical Analysis

Hodoodo Cat#: H540227
Name: Isoimperatorin
CAS#: 482-45-1
Chemical Formula: C16H14O4
Exact Mass: 270.09
Molecular Weight: 270.280
Elemental Analysis: C, 71.10; H, 5.22; O, 23.68

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 400	2 Weeks
100mg	USD 650	2 Weeks
250mg	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Iso-imperatorin

IUPAC/Chemical Name: 4-((3-methylbut-2-en-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one

InChi Key: IGWDEVSBEKYORK-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H14O4/c1-10(2)5-7-19-16-11-3-4-15(17)20-14(11)9-13-12(16)6-8-18-13/h3-6,8-9H,7H2,1-2H3

SMILES Code: O=C1C=CC2=C(OC/C=C(C)/C)C3=C(OC=C3)C=C2O1

Appearance: Solid powder

Purity: >95% (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

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 270.28 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:
In vitro protocol:
In vivo protocol:

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1: Guo N, Wu J, Fan J, Yuan P, Shi Q, Jin K, Cheng W, Zhao X, Zhang Y, Li W, Tang X, Yu L. In vitro activity of isoimperatorin, alone and in combination, against Mycobacterium tuberculosis. Lett Appl Microbiol. 2014 Apr;58(4):344-9. doi: 10.1111/lam.12195. Epub 2013 Dec 12. PubMed PMID: 24330002.

2: Chen TL, Zhang YB, Xu W, Kang TG, Yang XW. Biotransformation of isoimperatorin by rat liver microsomes and its quantification by LC-MS/MS method. Fitoterapia. 2014 Mar;93:88-97. doi: 10.1016/j.fitote.2013.12.017. Epub 2013 Dec 29. PubMed PMID: 24382450.

3: Shi X, Liu M, Zhang M, Zhang K, Liu S, Qiao S, Shi R, Jiang X, Wang Q. Identification of in vitro and in vivo metabolites of isoimperatorin using liquid chromatography/mass spectrometry. Food Chem. 2013 Nov 1;141(1):357-65. doi: 10.1016/j.foodchem.2013.02.068. Epub 2013 Feb 28. PubMed PMID: 23768368.

4: Cao J, Zheng L, Ji L, Lu D, Peng Y, Zheng J. Mechanism-based inactivation of cytochrome P450 2B6 by isoimperatorin. Chem Biol Interact. 2015 Jan 25;226:23-9. doi: 10.1016/j.cbi.2014.12.009. Epub 2014 Dec 11. PubMed PMID: 25500267.

5: Ranjbar S, Shokoohinia Y, Ghobadi S, Bijari N, Gholamzadeh S, Moradi N, Ashrafi-Kooshk MR, Aghaei A, Khodarahmi R. Studies of the interaction between isoimperatorin and human serum albumin by multispectroscopic method: identification of possible binding site of the compound using esterase activity of the protein. ScientificWorldJournal. 2013 Nov 10;2013:305081. doi: 10.1155/2013/305081. eCollection 2013. PubMed PMID: 24319355; PubMed Central PMCID: PMC3844181.

6: Li C, Wang CH, Zeng AG, Yang X, Yang GD. [Determination of supermolecular inclusion constants of hydroxylpropyl-beta-cylcodextrin with imperatorin and isoimperatorin by phase solubility method]. Zhong Yao Cai. 2011 Jun;34(6):965-7. Chinese. PubMed PMID: 22017013.

7: Chen J, Xu J, Xiong L. [Determination of imperatorin and isoimperatorin in cosmetics by high performance liquid chromatography-tandem mass spectrometry]. Se Pu. 2011 May;29(5):454-7. Chinese. PubMed PMID: 21847983.

8: Lili W, Yehong S, Qi Y, Yan H, Jinhui Z, Yan L, Cheng G. In vitro permeability analysis, pharmacokinetic and brain distribution study in mice of imperatorin, isoimperatorin and cnidilin in Radix Angelicae Dahuricae. Fitoterapia. 2013 Mar;85:144-53. doi: 10.1016/j.fitote.2013.01.007. Epub 2013 Jan 23. PubMed PMID: 23353658.

9: Cao Y, Zhong YH, Yuan M, Li H, Zhao CJ. [Inhibitory effect of imperatorin and isoimperatorin on activity of cytochrome P450 enzyme in human and rat liver microsomes]. Zhongguo Zhong Yao Za Zhi. 2013 Apr;38(8):1237-41. Chinese. PubMed PMID: 23944042.

10: Chang YX, Zhang QH, Li J, Zhang L, Guo XR, He J, Zhang P, Ma L, Deng YR, Zhang BL, Gao XM. Simultaneous determination of scopoletin, psoralen, bergapten, xanthotoxin, columbianetin acetate, imperatorin, osthole and isoimperatorin in rat plasma by LC-MS/MS for pharmacokinetic studies following oral administration of Radix Angelicae Pubescentis extract. J Pharm Biomed Anal. 2013 Apr 15;77:71-5. doi: 10.1016/j.jpba.2012.12.031. Epub 2013 Jan 5. PubMed PMID: 23384552.

11: Pokharel YR, Han EH, Kim JY, Oh SJ, Kim SK, Woo ER, Jeong HG, Kang KW. Potent protective effect of isoimperatorin against aflatoxin B1-inducible cytotoxicity in H4IIE cells: bifunctional effects on glutathione S-transferase and CYP1A. Carcinogenesis. 2006 Dec;27(12):2483-90. Epub 2006 Jul 8. PubMed PMID: 16829687.

12: Zhou Y, Jiang SY, Sun H, Yang AD, Ma Y, Ma XJ, Wu R. [Quantitative analysis of volatile oils and isoimperatorin in rhizoma et Radix notopterygii]. Zhongguo Zhong Yao Za Zhi. 2007 Apr;32(7):566-9. Chinese. PubMed PMID: 17583191.

13: Moon TC, Jin M, Son JK, Chang HW. The effects of isoimperatorin isolated from Angelicae dahuricae on cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Arch Pharm Res. 2008 Feb;31(2):210-5. PubMed PMID: 18365692.

14: Tong K, Xin C, Chen W. Isoimperatorin induces apoptosis of the SGC-7901 human gastric cancer cell line via the mitochondria-mediated pathway. Oncol Lett. 2017 Jan;13(1):518-524. doi: 10.3892/ol.2016.5387. Epub 2016 Nov 15. PubMed PMID: 28123591; PubMed Central PMCID: PMC5244867.

15: Moon L, Ha YM, Jang HJ, Kim HS, Jun MS, Kim YM, Lee YS, Lee DH, Son KH, Kim HJ, Seo HG, Lee JH, Kim YS, Chang KC. Isoimperatorin, cimiside E and 23-O-acetylshengmanol-3-xyloside from Cimicifugae rhizome inhibit TNF-α-induced VCAM-1 expression in human endothelial cells: involvement of PPAR-γ upregulation and PI3K, ERK1/2, and PKC signal pathways. J Ethnopharmacol. 2011 Jan 27;133(2):336-44. doi: 10.1016/j.jep.2010.10.004. Epub 2010 Oct 16. PubMed PMID: 20937376.

16: Marumoto S, Miyazawa M. Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity. Bioorg Med Chem. 2010 Jan 1;18(1):455-9. doi: 10.1016/j.bmc.2009.10.004. Epub 2009 Oct 8. PubMed PMID: 19939683.

17: Teye Azietaku J, Yu XA, Li J, Hao J, Cao J, An M, Tan Z, Chang YX. Simultaneous Determination of Bergapten, Imperatorin, Notopterol, and Isoimperatorin in Rat Plasma by High Performance Liquid Chromatography with Fluorescence Detection and Its Application to Pharmacokinetic and Excretion Study after Oral Administration of Notopterygium incisum Extract. Int J Anal Chem. 2016;2016:9507246. doi: 10.1155/2016/9507246. Epub 2016 Dec 26. PubMed PMID: 28115935; PubMed Central PMCID: PMC5220503.

18: Fu J, Dong X, Yin X, Yang C, Wang W, Du X, Zhang X, Ni J. A new polymorph of isoimperatorin. Pharm Dev Technol. 2017 Mar 16:1-8. doi: 10.1080/10837450.2016.1257023. [Epub ahead of print] PubMed PMID: 27808578.

19: Shi HL, Jia YW, Peng SL, Liao X, Ding LS, Liu YM. Metabolic study of Angelica dahurica extracts using a reusable liver microsomal nanobioreactor by liquid chromatography-mass spectrometry. Biomed Chromatogr. 2015 Oct;29(10):1514-1521. doi: 10.1002/bmc.3451. Epub 2015 Mar 8. PubMed PMID: 25753568; PubMed Central PMCID: PMC4562904.

20: Raza H, Abbas Q, Hassan M, Eo SH, Ashraf Z, Kim D, Phull AR, Kim SJ, Kang SK, Seo SY. Isolation, characterization, and in silico, in vitro and in vivo antiulcer studies of isoimperatorin crystallized from Ostericum koreanum. Pharm Biol. 2017 Dec;55(1):218-226. PubMed PMID: 27927061.

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Isoimperatorin featured