MedKoo Cat#: 122898 | Name: Pimpinellin
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Description:

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

Pimpinellin is a coumarin derivative that has been found in L. dasyanthus and has diverse biological activities. pimpinellin can specifically inhibit LPS-induced macrophage PARP1 and PAR activation. Pimpinellin inhibits collagen-induced ex vivo aggregation of mice platelets.

Chemical Structure

Pimpinellin
Pimpinellin
CAS#131-12-4

Theoretical Analysis

MedKoo Cat#: 122898

Name: Pimpinellin

CAS#: 131-12-4

Chemical Formula: C13H10O5

Exact Mass: 246.0500

Molecular Weight: 246.22

Elemental Analysis: C, 63.42; H, 4.09; O, 32.49

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 750.00 2 Weeks
25mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
pimpinellin; 131-12-4; Pimpinecilin
IUPAC/Chemical Name
5,6-dimethoxy-2H-furo[2,3-h]chromen-2-one
InChi Key
BQPRWZCEKZLBHL-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10O5/c1-15-11-7-3-4-9(14)18-10(7)8-5-6-17-12(8)13(11)16-2/h3-6H,1-2H3
SMILES Code
O=C1OC2=C(C(OC)=C(C3=C2C=CO3)OC)C=C1
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 246.22 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: Chishti AS, Uddin M, Singh S, Singh S, Bhat UH, Khan MMA. Exogenous application of salicylic acid and putrescine triggers physiological and biochemical changes in plants to improve growth and bioactive constituents of Ammi majus L. Fitoterapia. 2024 Jul 30;178:106148. doi: 10.1016/j.fitote.2024.106148. Epub ahead of print. PMID: 39089592. 2: Tao Y, Pu J, Wang P. Ethnobotany, phytochemistry, pharmacology and quality control of Peucedanum decursivum (Miq.) Maxim: A critical review. J Ethnopharmacol. 2024 Nov 15;334:118542. doi: 10.1016/j.jep.2024.118542. Epub 2024 Jul 9. PMID: 38992404. 3: Yang L, Du M, Liu K, Wang P, Zhu J, Li F, Wang Z, Huang K, Liang M. Pimpinellin ameliorates macrophage inflammation by promoting RNF146-mediated PARP1 ubiquitination. Phytother Res. 2024 Apr;38(4):1783-1798. doi: 10.1002/ptr.8135. Epub 2024 Feb 7. PMID: 38323338. 4: 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. 5: Olennikov DN. Coumarins of Lovage Roots (Levisticum officinale W.D.J.Koch): LC-MS Profile, Quantification, and Stability during Postharvest Storage. Metabolites. 2022 Dec 20;13(1):3. doi: 10.3390/metabo13010003. PMID: 36676932; PMCID: PMC9860584. 6: Kozioł E, Jóźwiak K, Budzyńska B, de Witte PAM, Copmans D, Skalicka-Woźniak K. Comparative Antiseizure Analysis of Diverse Natural Coumarin Derivatives in Zebrafish. Int J Mol Sci. 2021 Oct 22;22(21):11420. doi: 10.3390/ijms222111420. PMID: 34768849; PMCID: PMC8584229. 7: Qiu J, Zhu M, Wang Y, Chen B, Bai R, Chen F, Li Y, Zhou Y, Zhang L. Pharmacokinetic and excretion study of eight active constituents in rat by LC- MS/MS after oral administration of the Toddalia asiatica extract. Anal Biochem. 2022 Mar 1;640:114407. doi: 10.1016/j.ab.2021.114407. Epub 2021 Oct 9. PMID: 34637784. 8: Liu G, Yuan Z, Tian X, Xiong X, Guo F, Lin Z, Qin Z. Pimpinellin Inhibits Collagen-induced Platelet Aggregation and Activation Through Inhibiting Granule Secretion and PI3K/Akt Pathway. Front Pharmacol. 2021 Jul 22;12:706363. doi: 10.3389/fphar.2021.706363. PMID: 34366861; PMCID: PMC8339208. 9: Wang WH, Yan PZ, Yang B. [Study on fragmentation patterns of coumarins in Notopterygium inchum with ultrahigh performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry]. Zhongguo Zhong Yao Za Zhi. 2021 Mar;46(5):1179-1190. Chinese. doi: 10.19540/j.cnki.cjcmm.20201012.203. PMID: 33787113. 10: Karakaya S, Koca M, Yılmaz SV, Yıldırım K, Pınar NM, Demirci B, Brestic M, Sytar O. Molecular Docking Studies of Coumarins Isolated from Extracts and Essential Oils of Zosima absinthifolia Link as Potential Inhibitors for Alzheimer's Disease. Molecules. 2019 Feb 17;24(4):722. doi: 10.3390/molecules24040722. PMID: 30781573; PMCID: PMC6412260. 11: Ozek G, Yur S, Goger F, Ozek T, Andjelkovic B, Godjevac D, Sofrenic I, Aneva I, Todorova M, Trendafilova A. Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer's Disease and Type II Diabetes. Chem Biodivers. 2019 Apr;16(4):e1800672. doi: 10.1002/cbdv.201800672. Epub 2019 Mar 28. PMID: 30702800. 12: Karakaya S, Koca M, Sytar O, Duman H. The natural phenolic compounds and their antioxidant and anticholinesterase potential of herb Leiotulus dasyanthus (K. Koch) Pimenov & Ostr. Nat Prod Res. 2020 May;34(9):1303-1305. doi: 10.1080/14786419.2018.1557176. Epub 2019 Jan 18. PMID: 30657333. 13: Kviesis J, Kļimenkovs I, Arbidans L, Podjava A, Kļaviņš M, Liepiņš E. Evaluation of furanocoumarins from seeds of the wild parsnip (Pastinaca sativa L. s.l.). J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Jan 15;1105:54-66. doi: 10.1016/j.jchromb.2018.12.012. Epub 2018 Dec 12. PMID: 30562630. 14: Zhang X, Sun W, Yang Z, Liang Y, Zhou W, Tang L. Hemostatic chemical constituents from natural medicine Toddalia asiatica root bark by LC-ESI Q-TOF MSE. Chem Cent J. 2017 Jun 15;11(1):55. doi: 10.1186/s13065-017-0283-3. PMID: 29086834; PMCID: PMC5472640. 15: Li D, Wu L. Coumarins from the roots of Angelica dahurica cause anti- allergic inflammation. Exp Ther Med. 2017 Jul;14(1):874-880. doi: 10.3892/etm.2017.4569. Epub 2017 Jun 8. PMID: 28673013; PMCID: PMC5488689. 16: Zuo GY, Wang CJ, Han J, Li YQ, Wang GC. Synergism of coumarins from the Chinese drug Zanthoxylum nitidum with antibacterial agents against methicillin- resistant Staphylococcus aureus (MRSA). Phytomedicine. 2016 Dec 15;23(14):1814-1820. doi: 10.1016/j.phymed.2016.11.001. Epub 2016 Nov 5. PMID: 27912884. 17: Walasek M, Grzegorczyk A, Malm A, Skalicka-Woźniak K. Bioactivity-guided isolation of antimicrobial coumarins from Heracleum mantegazzianum Sommier & Levier (Apiaceae) fruits by high-performance counter-current chromatography. Food Chem. 2015 Nov 1;186:133-8. doi: 10.1016/j.foodchem.2015.02.011. Epub 2015 Feb 9. PMID: 25976802. 18: Liu ZG, Wang XY, Mao BP, Xie XL. [Study on chemical constituents of Toddalia asiatica]. Zhong Yao Cai. 2014 Sep;37(9):1600-3. Chinese. PMID: 25857161. 19: Wang S, Tang F, Yue Y, Yao X, Wei Q, Yu J. Simultaneous determination of 12 coumarins in bamboo leaves by HPLC. J AOAC Int. 2013 Sep-Oct;96(5):942-6. doi: 10.5740/jaoacint.12-441. PMID: 24282929. 20: Cervi A, Aillard P, Hazeri N, Petit L, Chai CL, Willis AC, Banwell MG. Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry. J Org Chem. 2013 Oct 4;78(19):9876-82. doi: 10.1021/jo401583q. Epub 2013 Sep 23. PMID: 23977955.