WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584151
CAS#: 82-02-0
Description: Khellin is a vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo.
Hodoodo Cat#: H584151
Name: Khellin
CAS#: 82-02-0
Chemical Formula: C14H12O5
Exact Mass: 260.07
Molecular Weight: 260.240
Elemental Analysis: C, 64.61; H, 4.65; O, 30.74
Synonym: Khellin; Amiptan; Benecardin; Chellin; Coronin; Eskel; Kelicor; Keloid; Khellin; Lynamine; Mefurina; Rykellin; Viscardan
IUPAC/Chemical Name: 4,9-Dimethoxy-7-methyl-5H-furo(3,2-g)(1)benzopyran-5-one
InChi Key: HSMPDPBYAYSOBC-UHFFFAOYSA-N
InChi Code: InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
SMILES Code: O=C1C=C(C)OC2=C(OC)C(OC=C3)=C3C(OC)=C12
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
More Info:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 260.24 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Fenniche S, Hammami H, Zaouak A. Association of khellin and 308-nm excimer lamp in the treatment of severe alopecia areata in a child. J Cosmet Laser Ther. 2017 Oct 11:1-3. doi: 10.1080/14764172.2017.1383617. [Epub ahead of print] PubMed PMID: 29020475.
2: Travaini ML, Sosa GM, Ceccarelli EA, Walter H, Cantrell CL, Carrillo NJ, Dayan FE, Meepagala KM, Duke SO. Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides. J Agric Food Chem. 2016 Dec 21;64(50):9475-9487. doi: 10.1021/acs.jafc.6b02462. Epub 2016 Dec 12. PubMed PMID: 27936681.
3: Kamal A, Khan W, Ahmad S, Ahmad FJ, Saleem K. Development and validation of high-performance liquid chromatography and high-performance thin-layer chromatography methods for the quantification of khellin in Ammi visnaga seed. J Pharm Bioallied Sci. 2015 Oct-Dec;7(4):308-13. doi: 10.4103/0975-7406.168033. PubMed PMID: 26681890; PubMed Central PMCID: PMC4678975.
4: Bagherani N. The efficacy of 308 nm UV excimer light as monotherapy and combination therapy with topical khellin 4% and/or tacrolimus 0.1% in the treatment of vitiligo. Dermatol Ther. 2016 Mar;29(2):137-8. doi: 10.1111/dth.12274. Epub 2015 Aug 17. PubMed PMID: 26279072.
5: Badr JM, Hadad GM, Nahriry K, Hassanean HA. Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations. Nat Prod Res. 2015;29(7):593-601. doi: 10.1080/14786419.2014.945170. Epub 2014 Aug 11. PubMed PMID: 25111086.
6: Vrzal R, Frauenstein K, Proksch P, Abel J, Dvorak Z, Haarmann-Stemmann T. Khellin and visnagin differentially modulate AHR signaling and downstream CYP1A activity in human liver cells. PLoS One. 2013 Sep 19;8(9):e74917. doi: 10.1371/journal.pone.0074917. eCollection 2013. PubMed PMID: 24069365; PubMed Central PMCID: PMC3777991.
7: Elgazwy AS, Edrees MM, Ismail NS. Molecular modeling study bioactive natural product of khellin analogues as a novel potential pharmacophore of EGFR inhibitors. J Enzyme Inhib Med Chem. 2013 Dec;28(6):1171-81. doi: 10.3109/14756366.2012.719504. Epub 2012 Oct 1. PubMed PMID: 23025406.
8: Hadad GM, Badr JM, El-Nahriry K, Hassanean HA. Validated HPLC and HPTLC methods for simultaneous determination of colchicine and khellin in pharmaceutical formulations. J Chromatogr Sci. 2013 Mar;51(3):258-65. doi: 10.1093/chromsci/bms135. Epub 2012 Aug 21. PubMed PMID: 22914568.
9: Abu-Hashem AA, Youssef MM. Synthesis of new visnagen and khellin furochromone pyrimidine derivatives and their anti-inflammatory and analgesic activity. Molecules. 2011 Feb 25;16(3):1956-72. doi: 10.3390/molecules16031956. PubMed PMID: 21358587.
10: Vanachayangkul P, Chow N, Khan SR, Butterweck V. Prevention of renal crystal deposition by an extract of Ammi visnaga L. and its constituents khellin and visnagin in hyperoxaluric rats. Urol Res. 2011 Jun;39(3):189-95. doi: 10.1007/s00240-010-0333-y. Epub 2010 Nov 11. PubMed PMID: 21069311; PubMed Central PMCID: PMC3663934.
11: de Leeuw J, Assen YJ, van der Beek N, Bjerring P, Martino Neumann HA. Treatment of vitiligo with khellin liposomes, ultraviolet light and blister roof transplantation. J Eur Acad Dermatol Venereol. 2011 Jan;25(1):74-81. doi: 10.1111/j.1468-3083.2010.03701.x. PubMed PMID: 20477914.
12: Vanachayangkul P, Byer K, Khan S, Butterweck V. An aqueous extract of Ammi visnaga fruits and its constituents khellin and visnagin prevent cell damage caused by oxalate in renal epithelial cells. Phytomedicine. 2010 Jul;17(8-9):653-8. doi: 10.1016/j.phymed.2009.10.011. Epub 2009 Dec 29. PubMed PMID: 20036111; PubMed Central PMCID: PMC3618668.
13: Omar S, Eriksson LA. Computational study of khellin excited states and photobinding to DNA. Photochem Photobiol Sci. 2009 Aug;8(8):1179-86. doi: 10.1039/b905147c. Epub 2009 Jul 6. PubMed PMID: 19639121.
14: Saraceno R, Nisticò SP, Capriotti E, Chimenti S. Monochromatic excimer light 308 nm in monotherapy and combined with topical khellin 4% in the treatment of vitiligo: a controlled study. Dermatol Ther. 2009 Jul-Aug;22(4):391-4. doi: 10.1111/j.1529-8019.2009.01252.x. PubMed PMID: 19580584.
15: Fersi H, Platz MS. Nanosecond time-resolved infrared studies of visnagin and khellin triplets and radical ions. J Phys Chem A. 2005 Oct 20;109(41):9206-12. PubMed PMID: 16833259.
16: El-Gogary S, Grabner G. Ultraviolet photoionization of the photosensitizers khellin and visnagin in aqueous solution and in micelles: one-photon ionization is a minor process. Photochem Photobiol Sci. 2006 Mar;5(3):311-6. Epub 2006 Jan 11. PubMed PMID: 16520866.
17: Capella GL. Topical khellin and natural sunlight in the outpatient treatment of recalcitrant palmoplantar pompholyx: report of an open pilot study. Dermatology. 2005;211(4):381-3. PubMed PMID: 16286756.
18: Valkova S, Trashlieva M, Christova P. Treatment of vitiligo with local khellin and UVA: comparison with systemic PUVA. Clin Exp Dermatol. 2004 Mar;29(2):180-4. PubMed PMID: 14987278.
19: de Leeuw J, van der Beek N, Maierhofer G, Neugebauer WD. A case study to evaluate the treatment of vitiligo with khellin encapsulated in L-phenylalanin stabilized phosphatidylcholine liposomes in combination with ultraviolet light therapy. Eur J Dermatol. 2003 Sep-Oct;13(5):474-7. PubMed PMID: 14693493.
20: Carlie G, Ntusi NB, Hulley PA, Kidson SH. KUVA (khellin plus ultraviolet A) stimulates proliferation and melanogenesis in normal human melanocytes and melanoma cells in vitro. Br J Dermatol. 2003 Oct;149(4):707-17. PubMed PMID: 14616361.
