Geiparvarin | CAS#36413-91-9 | biochemical

MedKoo Cat#: 146225 | Name: Geiparvarin

Description:

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

Geiparvarin is a naturally occurring coumarin derivative isolated from the plant Geijera parviflora. It has been studied for its antitumor, anticoagulant, and anti-inflammatory properties, with particular interest in its potential as a lead compound for anticancer drug development. Geiparvarin's mechanism of action is thought to involve inhibition of monoamine oxidase (MAO) and interference with mitochondrial function, leading to the induction of apoptosis in cancer cells. Its ability to modulate cellular redox states and enzyme activity makes it a valuable candidate in pharmacological research.

Chemical Structure

Geiparvarin

CAS#36413-91-9

Theoretical Analysis

MedKoo Cat#: 146225

Name: Geiparvarin

CAS#: 36413-91-9

Chemical Formula: C15H10O5

Exact Mass: 270.0528

Molecular Weight: 270.24

Elemental Analysis: C, 66.67; H, 3.73; O, 29.60

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

Geiparvarin;

IUPAC/Chemical Name

(E)-7-((3-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)but-2-en-1-yl)oxy)-2H-chromen-2-one

InChi Key

OUTLLBZGJYDUQE-XYOKQWHBSA-N

InChi Code

1S/C19H18O5/c1-12(15-11-17(20)19(2,3)24-15)8-9-22-14-6-4-13-5-7-18(21)23-16(13)10-14/h4-8,10-11H,9H2,1-3H3/b12-8+

SMILES Code

C\C(=C/COC1=CC2=C(C=CC(=O)O2)C=C1)C3=CC(=O)C(C)(C)O3

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 270.24 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

1: Wang B, Du J, Zhang Z, Huang P, Chen S, Zou H. Geiparvarin Inhibits the Progression of Osteosarcoma by Down-regulating COX2 Expression. Curr Cancer Drug Targets. 2023;23(5):379-387. doi: 10.2174/1568009623666221208113432. PMID: 36503472. 2: Jiang F, Wang GJ, Huang P, Chen S, Xiao H, Zhang L, Zou H. Geiparvarin Inhibits OS Metastasis through Upregulation of ANGPTL4 Expression by Inhibiting miRNA-3912-3p Expression. Evid Based Complement Alternat Med. 2022 Apr 12;2022:4663684. doi: 10.1155/2022/4663684. PMID: 35463073; PMCID: PMC9019413. 3: Patel DK. Biological Potential and Therapeutic Effectiveness of Geiparvarin in Medicine for its Anti-proliferative Activity against Tumors and Other Human Complications. Curr Drug Targets. 2023;24(16):1221-1223. doi: 10.2174/0113894501271142231120065852. PMID: 38037997. 4: Simoni D, Manfredini S, Tabrizi MA, Bazzanini R, Baraldi PG, Balzarini J, De Clercq E. Geiparvarin analogues. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates. J Med Chem. 1991 Nov;34(11):3172-6. doi: 10.1021/jm00115a004. PMID: 1956034. 5: Miglietta A, Bocca C, Rampa A, Bisi A, Gabriel L. Geiparvarin and derivatives in combination with taxol: effect on microtubular organization in 3T3 fibroblasts. Anticancer Drug Des. 1997 Dec;12(8):607-20. PMID: 9448701. 6: Chimichi S, Boccalini M, Salvador A, Dall'Acqua F, Basso G, Viola G. Synthesis and biological evaluation of new geiparvarin derivatives. ChemMedChem. 2009 May;4(5):769-79. doi: 10.1002/cmdc.200900009. PMID: 19322800. 7: Valenti P, Rampa A, Bisi A, Belluti F, Da Re P, Carrara M, Cima L. Some geiparvarin bioisosteres and homologues: synthesis and biological evaluation against human colon carcinoma cells (LoVo). Anticancer Drug Des. 1997 Mar;12(2):137-44. PMID: 9113068. 8: Viola G, Vedaldi D, dall'Acqua F, Basso G, Disarò S, Spinelli M, Cosimelli B, Boccalini M, Chimichi S. Synthesis, cytotoxicity, and apoptosis induction in human tumor cells by geiparvarin analogues. Chem Biodivers. 2004 Sep;1(9):1265-80. doi: 10.1002/cbdv.200490089. PMID: 17191904. 9: Miglietta A, Bocca C, Gabriel L, Rampa A, Bisi A, Valenti P. Antimicrotubular and cytotoxic activity of geiparvarin analogues, alone and in combination with paclitaxel. Cell Biochem Funct. 2001 Sep;19(3):181-9. doi: 10.1002/cbf.919. PMID: 11494307. 10: Miglietta A, Bocca C, Gadoni E, Gabriel L, Rampa A, Bisi A, Valenti P, Da Re P. Interaction of geiparvarin and related compounds with purified microtubular protein. Anticancer Drug Des. 1996 Jan;11(1):35-48. PMID: 8639247. 11: Baraldi PG, Manfredini S, Simoni D, Tabrizi MA, Balzarini J, De Clercq E. Geiparvarin analogues. 3. Synthesis and cytostatic activity of 3(2H)-furanone and 4,5-dihydro-3(2H)-furanone congeners of geiparvarin, containing a geraniol- like fragment in the side chain. J Med Chem. 1992 May 15;35(10):1877-82. doi: 10.1021/jm00088a025. PMID: 1588564. 12: Valenti P, Recanatini M, Da Re P, Galimbeni W, Avanzi N, Filippeschi S. Xanthone analogue of geiparvarin. Arch Pharm (Weinheim). 1985 Oct;318(10):923-6. doi: 10.1002/ardp.19853181012. PMID: 4084022. 13: Zhang Y, Lv Z, Zhong H, Geng D, Zhang M, Zhang T, Li Y, Li K. Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry. Eur J Med Chem. 2012 Jul;53:356-63. doi: 10.1016/j.ejmech.2012.04.026. Epub 2012 Apr 26. PMID: 22579780. 14: Bocca C, Gabriel L, Miglietta A. Cytoskeleton-interacting activity of geiparvarin, diethylstilbestrol and conjugates. Chem Biol Interact. 2001 Sep 28;137(3):285-305. doi: 10.1016/s0009-2797(01)00261-7. PMID: 11566295. 15: Valenti P, Da Re P, Rampa A, Montanari P, Carrara M, Cima L. Benzo-gamma- pyrone analogues of geiparvarin: synthesis and biological evaluation against B16 melanoma cells. Anticancer Drug Des. 1993 Oct;8(5):349-60. PMID: 8251042. 16: Baraldi PG, Guarneri M, Manfredini S, Simoni D, Balzarini J, De Clercq E. Synthesis and cytostatic activity of geiparvarin analogues. J Med Chem. 1989 Feb;32(2):284-8. doi: 10.1021/jm00122a002. PMID: 2913291. 17: Carotti A, Carrieri A, Chimichi S, Boccalini M, Cosimelli B, Gnerre C, Carotti A, Carrupt PA, Testa B. Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. Synthesis and SAR studies. Bioorg Med Chem Lett. 2002 Dec 16;12(24):3551-5. doi: 10.1016/s0960-894x(02)00798-9. PMID: 12443774. 18: Manfredini S, Baraldi PG, Bazzanini R, Guarneri M, Simoni D, Balzarini J, De Clercq E. Geiparvarin analogues. 4. Synthesis and cytostatic activity of geiparvarin analogues bearing a carbamate moiety or a furocoumarin fragment on the alkenyl side chain. J Med Chem. 1994 Jul 22;37(15):2401-5. doi: 10.1021/jm00041a019. PMID: 8057288. 19: Valenti P, Rampa A, Recanatini M, Bisi A, Belluti F, Da Re P, Carrara M, Cima L. Synthesis, cytotoxicity and SAR of simple geiparvarin analogues. Anticancer Drug Des. 1997 Sep;12(6):443-51. PMID: 9311554. 20: Dugan D, Bell RJ, Brkljača R, Rix C, Taki AC, Gasser RB, Urban S. Phytochemical Profiling Studies of Alkaloids and Coumarins from the Australian Plant Geijera parviflora Lindl. (Rutaceae) and Their Anthelmintic and Antimicrobial Assessment. Metabolites. 2024 Apr 30;14(5):259. doi: 10.3390/metabo14050259. PMID: 38786736; PMCID: PMC11123165.