Imperatorin | Pentosalen | CAS#482-44-0

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

MedKoo CAT#: 328060

CAS#: 482-44-0

Description: Imperatorin, aslo known as Pentosalen, Marmelosin, is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica, etc. Imperatorin has many documented pharmacological properties which make it a candidate for possible drug development. Imperatorin showed the activity on the central nervous system, anticancer and antiviral, and the cardiovascular system.

Chemical Structure

Imperatorin

CAS# 482-44-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 328060
Name: Imperatorin
CAS#: 482-44-0
Chemical Formula: C16H14O4
Exact Mass: 270.09
Molecular Weight: 270.284
Elemental Analysis: C, 71.10; H, 5.22; O, 23.68

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 450
100mg	USD 750
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. MedKoo 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: Imperatorin; Pentosalen; Ammidin; Marmelosin

IUPAC/Chemical Name: 9-[(3-Methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one

InChi Key: OLOOJGVNMBJLLR-UHFFFAOYSA-N

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

SMILES Code: O=C1C=CC2=CC3=C(OC=C3)C(OC/C=C(C)/C)=C2O1

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

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Biological target:	Imperatorin is an effective of NO synthesis inhibitor (IC50=9.2 μmol), which also is a BChE inhibitor (IC50=31.4 μmol). Imperatorin is a weak agonist of TRPV1 with EC50 of 12.6±3.2 μM.
In vitro activity:	Imperatorin also activated the expression of melanogenic enzymes, such as tyrosinase (TYR) and tyrosinase-related proteins TYRP-1 and TYRP-2. Mechanistically, imperatorin increases melanin synthesis through the cyclic adenosine monophosphate (cAMP)-dependent protein kinase (PKA)/cAMP-responsive element-binding protein (CREB)-dependent upregulation of microphthalmia-associated transcription factor (MITF), which is a key transcription factor in melanogenesis. Furthermore, imperatorin exerted melanogenic effects by downregulating extracellular signal-regulated kinase (ERK) and upregulating phosphatidylinositol 3 kinase (PI3K)/protein kinase B (AKT)/glycogen synthesis kinase-3β (GSK-3β). Moreover, imperatorin increased the content of β-catenin in the cell cytoplasm and nucleus by reducing the content of phosphorylated β-catenin (p-β-catenin). Reference: Molecules. 2022 Oct 2;27(19):6512. https://pubmed.ncbi.nlm.nih.gov/36235048/
In vivo activity:	The study revealed that only males responded to imperatorin (1 and 5 mg/kg) treatment and caused an antidepressant effect, such as with respect to depressive-like behaviors, lowering immobility time and increasing immobility latency. Reference: Molecules. 2022 Feb 10;27(4):1179. https://pubmed.ncbi.nlm.nih.gov/35208969/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	110.99
	DMF:PBS (pH 7.2) (1:3)	0.3	0.92
	DMSO	41.3	152.93
	Ethanol	10.0	37.00

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:	1. Kim T, Hyun CG. Imperatorin Positively Regulates Melanogenesis through Signaling Pathways Involving PKA/CREB, ERK, AKT, and GSK3β/β-Catenin. Molecules. 2022 Oct 2;27(19):6512. doi: 10.3390/molecules27196512. PMID: 36235048; PMCID: PMC9571183. 2. Lin W, Chen G, Mao Y, Ma X, Zhou J, Yu X, Wang C, Liu M. Imperatorin Inhibits Proliferation, Migration, and Inflammation via Blocking the NF-κB and MAPK Pathways in Rheumatoid Fibroblast-like Synoviocytes. ACS Omega. 2022 Aug 16;7(34):29868-29876. doi: 10.1021/acsomega.2c02766. PMID: 36061691; PMCID: PMC9434770. 3. Kowalczyk J, Nakos-Bimpos M, Polissidis A, Dalla C, Kokras N, Skalicka-Woźniak K, Budzyńska B. Imperatorin Influences Depressive-like Behaviors: A Preclinical Study on Behavioral and Neurochemical Sex Differences. Molecules. 2022 Feb 10;27(4):1179. doi: 10.3390/molecules27041179. PMID: 35208969; PMCID: PMC8875245. 4. Lv M, Xu Q, Zhang B, Yang Z, Xie J, Guo J, He F, Wang W. Imperatorin induces autophagy and G0/G1 phase arrest via PTEN-PI3K-AKT-mTOR/p21 signaling pathway in human osteosarcoma cells in vitro and in vivo. Cancer Cell Int. 2021 Dec 19;21(1):689. doi: 10.1186/s12935-021-02397-7. PMID: 34923996; PMCID: PMC8684670.
In vitro protocol:	1. Kim T, Hyun CG. Imperatorin Positively Regulates Melanogenesis through Signaling Pathways Involving PKA/CREB, ERK, AKT, and GSK3β/β-Catenin. Molecules. 2022 Oct 2;27(19):6512. doi: 10.3390/molecules27196512. PMID: 36235048; PMCID: PMC9571183. 2. Lin W, Chen G, Mao Y, Ma X, Zhou J, Yu X, Wang C, Liu M. Imperatorin Inhibits Proliferation, Migration, and Inflammation via Blocking the NF-κB and MAPK Pathways in Rheumatoid Fibroblast-like Synoviocytes. ACS Omega. 2022 Aug 16;7(34):29868-29876. doi: 10.1021/acsomega.2c02766. PMID: 36061691; PMCID: PMC9434770.
In vivo protocol:	1. Kowalczyk J, Nakos-Bimpos M, Polissidis A, Dalla C, Kokras N, Skalicka-Woźniak K, Budzyńska B. Imperatorin Influences Depressive-like Behaviors: A Preclinical Study on Behavioral and Neurochemical Sex Differences. Molecules. 2022 Feb 10;27(4):1179. doi: 10.3390/molecules27041179. PMID: 35208969; PMCID: PMC8875245. 2. Lv M, Xu Q, Zhang B, Yang Z, Xie J, Guo J, He F, Wang W. Imperatorin induces autophagy and G0/G1 phase arrest via PTEN-PI3K-AKT-mTOR/p21 signaling pathway in human osteosarcoma cells in vitro and in vivo. Cancer Cell Int. 2021 Dec 19;21(1):689. doi: 10.1186/s12935-021-02397-7. PMID: 34923996; PMCID: PMC8684670.

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1: Hu L, Sun J, Li H, Wang L, Wei Y, Wang Y, Zhu Y, Huo H, Tan Y. Differential mechanistic investigation of protective effects from imperatorin and sec-O-glucosylhamaudol against arsenic trioxide-induced cytotoxicity in vitro. Toxicol In Vitro. 2016 Dec;37:97-105. doi: 10.1016/j.tiv.2016.09.002. PubMed PMID: 27608960.

2: Jia M, Li Y, Xin HL, Hou TT, Zhang ND, Xu HT, Zhang QY, Qin LP. Estrogenic activity of osthole and imperatorin in MCF-7 cells and their osteoblastic effects in Saos-2 cells. Chin J Nat Med. 2016 Jun;14(6):413-20. doi: 10.1016/S1875-5364(16)30037-1. PubMed PMID: 27473958.

3: Kozioł E, Skalicka-Woźniak K. Imperatorin-pharmacological meaning and analytical clues: profound investigation. Phytochem Rev. 2016;15:627-649. Review. PubMed PMID: 27453708; PubMed Central PMCID: PMC4939159.

4: Lee E, Choi SY, Yang JH, Lee YJ. Preventive effects of imperatorin on perfluorohexanesulfonate-induced neuronal apoptosis via inhibition of intracellular calcium-mediated ERK pathway. Korean J Physiol Pharmacol. 2016 Jul;20(4):399-406. doi: 10.4196/kjpp.2016.20.4.399. PubMed PMID: 27382356; PubMed Central PMCID: PMC4930908.

5: Lin CL, Hsiao G, Wang CC, Lee YL. Imperatorin exerts antiallergic effects in Th2-mediated allergic asthma via induction of IL-10-producing regulatory T cells by modulating the function of dendritic cells. Pharmacol Res. 2016 Aug;110:111-21. doi: 10.1016/j.phrs.2016.04.030. PubMed PMID: 27185659.

6: Zhou N, Zhu Y, Zhang P, Zhang YU, Zhou M, Wang T, He L. Imperatorin derivative OW1 inhibits the upregulation of TGF-β and MMP-2 in renovascular hypertension-induced cardiac remodeling. Exp Ther Med. 2016 May;11(5):1748-1754. PubMed PMID: 27168797; PubMed Central PMCID: PMC4840669.

7: Song G, Jin M, Du Y, Cao L, Xu H. UPLC-QTOF-MS/MS based screening and identification of the metabolites in rat bile after oral administration of imperatorin. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jun 1;1022:21-9. doi: 10.1016/j.jchromb.2016.04.007. PubMed PMID: 27070117.

8: Ouyang P, Chen J, Sun M, Yin Z, Lin J, Fu H, Shu G, He C, Lv C, Deng X, Wang K, Geng Y, Yin L. Imperatorin inhibits the expression of alpha-hemolysin in Staphylococcus aureus strain BAA-1717 (USA300). Antonie Van Leeuwenhoek. 2016 Jul;109(7):915-22. doi: 10.1007/s10482-016-0690-9. PubMed PMID: 27043440.

9: Zheng YM, Lu AX, Shen JZ, Kwok AH, Ho WS. Imperatorin exhibits anticancer activities in human colon cancer cells via the caspase cascade. Oncol Rep. 2016 Apr;35(4):1995-2002. doi: 10.3892/or.2016.4586. PubMed PMID: 26794238.

10: Hwang YL, Im M, Lee MH, Roh SS, Choi BW, Kim SJ, Sohn KC, Lee Y, Seo YJ, Lee JH, Kim CD. Inhibitory effect of imperatorin on insulin-like growth factor-1-induced sebum production in human sebocytes cultured in vitro. Life Sci. 2016 Jan 1;144:49-53. doi: 10.1016/j.lfs.2015.11.027. PubMed PMID: 26631504.

11: Jeong KT, Lee E, Park NY, Kim SG, Park HH, Lee J, Lee YJ, Lee E. Imperatorin Suppresses Degranulation and Eicosanoid Generation in Activated Bone Marrow-Derived Mast Cells. Biomol Ther (Seoul). 2015 Sep;23(5):421-7. doi: 10.4062/biomolther.2015.023. PubMed PMID: 26336581; PubMed Central PMCID: PMC4556201.

12: Mendel M, Skalicka-Woźniak K, Chłopecka M, Dziekan N. Effect of Imperatorin on the Spontaneous Motor Activity of Rat Isolated Jejunum Strips. Evid Based Complement Alternat Med. 2015;2015:614849. doi: 10.1155/2015/614849. PubMed PMID: 26236380; PubMed Central PMCID: PMC4510122.

13: Hu J, Xu C, Cheng B, Jin L, Li J, Gong Y, Lin W, Pan Z, Pan C. Imperatorin acts as a cisplatin sensitizer via downregulating Mcl-1 expression in HCC chemotherapy. Tumour Biol. 2016 Jan;37(1):331-9. doi: 10.1007/s13277-015-3591-z. PubMed PMID: 26219890.

14: Zhou N, Zhang Y, Wang T, He J, He H, He L. The imperatorin derivative OW1, a new vasoactive compound, inhibits VSMC proliferation and extracellular matrix hyperplasia. Toxicol Appl Pharmacol. 2015 Apr 15;284(2):125-33. doi: 10.1016/j.taap.2015.02.019. PubMed PMID: 25727310.

15: Correction to: "Imperatorin is a mechanism-based inactivator of CYP2B6". Drug Metab Dispos. 2015 Apr;43(4):570. doi: 10.1124/dmd.115.060558err. PubMed PMID: 25713273.

16: Wang YW, Yang CT, Chen YH, Gong CL, Chen YF, Kuo YH, Leung YM. Inhibitory effects of imperatorin on voltage-gated K(+) channels and ATP-sensitive K(+) channels. Pharmacol Rep. 2015 Feb;67(1):134-9. doi: 10.1016/j.pharep.2014.08.015. PubMed PMID: 25560587.

17: Zheng L, Cao J, Lu D, Ji L, Peng Y, Zheng J. Imperatorin is a mechanism-based inactivator of CYP2B6. Drug Metab Dispos. 2015 Jan;43(1):82-8. doi: 10.1124/dmd.114.060558. Erratum in: Drug Metab Dispos. 2015 Apr;43(4):570. PubMed PMID: 25378064.

18: Rahman A, Siddiqui SA, Jakhar R, Kang SC. Growth inhibition of various human cancer cell lines by imperatorin and limonin from poncirus trifoliata rafin. Seeds. Anticancer Agents Med Chem. 2015;15(2):236-41. PubMed PMID: 25244913.

19: Budzynska B, Boguszewska-Czubara A, Kruk-Slomka M, Skalicka-Wozniak K, Michalak A, Musik I, Biala G. Effects of imperatorin on scopolamine-induced cognitive impairment and oxidative stress in mice. Psychopharmacology (Berl). 2015 Mar;232(5):931-42. doi: 10.1007/s00213-014-3728-6. PubMed PMID: 25189792; PubMed Central PMCID: PMC4325182.

20: Cao Y, Zhang Y, Wang N, He L. Antioxidant effect of imperatorin from Angelica dahurica in hypertension via inhibiting NADPH oxidase activation and MAPK pathway. J Am Soc Hypertens. 2014 Aug;8(8):527-36. doi: 10.1016/j.jash.2014.04.006. PubMed PMID: 24973900.

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