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MedKoo Cat#: 146319 | Name: Phellopterin

Description:

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

Phellopterin is a naturally occurring furanocoumarin compound found in plants such as Angelica dahurica and Poncirus trifoliata. It exhibits a range of biological activities, including anti-inflammatory, antimicrobial, and potential anticancer effects. The compound functions by modulating various cellular pathways, such as inhibiting the adhesion of monocytes to endothelial cells through the regulation of the Akt and PKC signaling pathways . Additionally, phellopterin has been shown to interact with GABA receptors and may influence the activity of cytochrome P450 enzymes .

Chemical Structure

Phellopterin
Phellopterin
CAS#2543-94-4

Theoretical Analysis

MedKoo Cat#: 146319

Name: Phellopterin

CAS#: 2543-94-4

Chemical Formula: C17H16O5

Exact Mass: 300.0998

Molecular Weight: 300.31

Elemental Analysis: C, 67.99; H, 5.37; O, 26.64

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
Phellopterin;
IUPAC/Chemical Name
4-methoxy-9-((3-methylbut-2-en-1-yl)oxy)-7H-furo[3,2-g]chromen-7-one
InChi Key
BMLZFLQMBMYVHG-UHFFFAOYSA-N
InChi Code
1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3
SMILES Code
COC1=C2C=CC(=O)OC2=C(OCC=C(C)C)C3=C1C=CO3
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 300.31 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: Zou J, Duan Y, Wang Y, Liu A, Chen Y, Guo D, Guo W, Li S, Su Z, Wu Y, Lu H, Deng Y, Zhu J, Li F. Phellopterin cream exerts an anti-inflammatory effect that facilitates diabetes-associated cutaneous wound healing via SIRT1. Phytomedicine. 2022 Dec;107:154447. doi: 10.1016/j.phymed.2022.154447. Epub 2022 Sep 20. PMID: 36150345. 2: Guo A, Lin J, Zhong P, Chen J, Wang L, Lin X, Feng M. Phellopterin attenuates ovarian cancer proliferation and chemoresistance by inhibiting the PU.1/CLEC5A/PI3K-AKT feedback loop. Toxicol Appl Pharmacol. 2023 Oct 15;477:116691. doi: 10.1016/j.taap.2023.116691. Epub 2023 Sep 12. PMID: 37708916. 3: Chen X, Zhang Y, Pei J, Zeng X, Yang Y, Zhang Y, Li F, Deng Y. Phellopterin alleviates atopic dermatitis-like inflammation and suppresses IL-4-induced STAT3 activation in keratinocytes. Int Immunopharmacol. 2022 Nov;112:109270. doi: 10.1016/j.intimp.2022.109270. Epub 2022 Sep 28. PMID: 36179418. 4: Han HS, Jeon H, Kang SC. Phellopterin isolated from Angelica dahurica reduces blood glucose level in diabetic mice. Heliyon. 2018 Mar 19;4(3):e00577. doi: 10.1016/j.heliyon.2018.e00577. PMID: 29862342; PMCID: PMC5968131. 5: Xu X, Su Y, Pan Y, Shen M, Liu D, Liu Z, Chen D, Wu J. The therapeutic effect of phellopterin on colitis-associated cancer and its effects on TLR4/NF-κB pathway and macrophage M2 polarization. Cell Mol Biol (Noisy-le-grand). 2023 Dec 31;69(15):51-57. doi: 10.14715/cmb/2023.69.15.8. PMID: 38279493. 6: Cheng Z, He Y, Chen Y, Zhao G, Liu Y, Zhang J, Li X, Ran G, Zhang Q, Peng Y, Li W, Zheng J. Mechanism-Based Inactivation of CYP2D6 by Phellopterin and Related Drug-Drug Interaction with Metoprolol. J Agric Food Chem. 2024 Jan 24;72(3):1745-1755. doi: 10.1021/acs.jafc.3c07356. Epub 2024 Jan 12. PMID: 38214270. 7: Nakamura M, Suzuki T, Takagi M, Tamura H, Masuda T. Stimulation of phosphorylation of ERK and CREB by phellopterin and auraptene isolated from Citrusjunos. Nat Prod Commun. 2014 Oct;9(10):1491-4. PMID: 25522543. 8: Zhao AH, Yang XB, Yang XW, Zhang YB, Xu W, Liu JX. Biotransformation products of phellopterin by rat liver microsomes and the inhibition on NO production in LPS-activated RAW264.7 cells. J Asian Nat Prod Res. 2012;14(10):956-65. doi: 10.1080/10286020.2012.729506. PMID: 23046467. 9: Nizamutdinova IT, Jeong JJ, Xu GH, Lee SH, Kang SS, Kim YS, Chang KC, Kim HJ. Hesperidin, hesperidin methyl chalone and phellopterin from Poncirus trifoliata (Rutaceae) differentially regulate the expression of adhesion molecules in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells. Int Immunopharmacol. 2008 May;8(5):670-8. doi: 10.1016/j.intimp.2008.01.011. Epub 2008 Feb 8. PMID: 18387509. 10: Li L, Chen J, Yang X, Zhang Y, Yang D. In vivo metabolite profiles of isoimperatorin and phellopterin in rats analyzed using HPLC coupled with diode array detector and electrospray ionization ion trap time-of-flight mass spectrometry technique. Biomed Chromatogr. 2018 Aug;32(8):e4236. doi: 10.1002/bmc.4236. Epub 2018 Apr 26. PMID: 29516524. 11: Dekermendjian K, Ai J, Nielsen M, Sterner O, Shan R, Witt MR. Characterisation of the furanocoumarin phellopterin as a rat brain benzodiazepine receptor partial agonist in vitro. Neurosci Lett. 1996 Nov 29;219(3):151-4. doi: 10.1016/s0304-3940(96)13183-9. PMID: 8971802. 12: Liu Z, Jiang M, Lu X, Qin F, Song Y, Wen J, Li F. Simultaneous determination of pimpinellin, isopimpinellin and phellopterin in rat plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of Toddalia asiatica extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Apr 1;891-892:102-8. doi: 10.1016/j.jchromb.2012.02.022. Epub 2012 Feb 22. PMID: 22418072. 13: Azietaku JT, Ma H, Yu XA, Li J, Oppong MB, Cao J, An M, Chang YX. A review of the ethnopharmacology, phytochemistry and pharmacology of Notopterygium incisum. J Ethnopharmacol. 2017 Apr 18;202:241-255. doi: 10.1016/j.jep.2017.03.022. Epub 2017 Mar 21. PMID: 28336469. 14: Heinke R, Franke K, Porzel A, Wessjohann LA, Ali NA, Schmidt J. Furanocoumarins from Dorstenia foetida. Phytochemistry. 2011 Jun;72(9):929-34. doi: 10.1016/j.phytochem.2011.03.008. Epub 2011 Apr 12. PMID: 21492886. 15: Zhang Y, Hou M, Yu Y, Xie W, Chang R, Zhang G, Zhang H, Yu H, Chen A. Simultaneous separation and determination of six furanocoumarins in Radix Angelicae dahuricae by CZE with dual CDs system. Anal Biochem. 2022 Oct 15;655:114869. doi: 10.1016/j.ab.2022.114869. Epub 2022 Aug 19. PMID: 35988798. 16: Bartnik M. Methoxyfuranocoumarins of Natural Origin-Updating Biological Activity Research and Searching for New Directions-A Review. Curr Issues Mol Biol. 2024 Jan 19;46(1):856-883. doi: 10.3390/cimb46010055. PMID: 38275669; PMCID: PMC10813879. 17: Cox PJ, Jaspars M, Kumarasamy Y, Nahar L, Sarker SD, Shoeb M. A mixed crystal of imperatorin and phellopterin, with C--H...O, C--H...pi and pi-pi interactions. Acta Crystallogr C. 2003 Sep;59(Pt 9):o520-2. doi: 10.1107/s0108270103012459. Epub 2003 Aug 16. PMID: 12944664. 18: Xin XL, Wang Y, Wang G, Wang C, Huang SS, Huo XK, Su DH, Tian XG. Biotransformation of furanocoumarins by fungi: preparation of imperation analogs. J Asian Nat Prod Res. 2018 Jul;20(7):697-707. doi: 10.1080/10286020.2016.1268601. Epub 2017 Jan 31. PMID: 28140678. 19: Song PP, Lv Y, Xu ZL, Wang Q, Wang NH. [Chemical constituents of Angelica nitida roots]. Zhong Yao Cai. 2014 Jan;37(1):55-7. Chinese. PMID: 25090703. 20: Adebajo AC, Reisch J. Minor furocoumarins of Murraya koenigii. Fitoterapia. 2000 Jun;71(3):334-7. doi: 10.1016/s0367-326x(99)00163-x. PMID: 10844176.