Khellactone | CAS#518-76-3 | biochemical

MedKoo Cat#: 145754 | Name: Khellactone

Description:

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

Khellactone is a natural compound found in certain plants, notably from the Ammi visnaga plant, which belongs to the Apiaceae family. It is a type of furanocoumarin, a group of chemical compounds known for their biological activity. Khellactone has been studied for its potential therapeutic effects, particularly in the areas of vasodilation and smooth muscle relaxation, which may be beneficial in treating conditions like asthma or vascular diseases. Additionally, it has shown some potential as an anti-inflammatory and antioxidant agent.

Chemical Structure

Khellactone

CAS#518-76-3

Theoretical Analysis

MedKoo Cat#: 145754

Name: Khellactone

CAS#: 518-76-3

Chemical Formula: C14H14O5

Exact Mass: 262.0800

Molecular Weight: 262.26

Elemental Analysis: C, 64.12; H, 5.38; O, 30.50

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

Khellactone;

IUPAC/Chemical Name

9,10-dihydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one

InChi Key

HKXQUNNSKMWIKJ-UHFFFAOYSA-N

InChi Code

1S/C14H14O5/c1-14(2)13(17)11(16)10-8(19-14)5-3-7-4-6-9(15)18-12(7)10/h3-6,11,13,16-17H,1-2H3

SMILES Code

CC1(C)OC2=CC=C3C=CC(=O)OC3=C2C(O)C1O

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 262.26 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: Feng L, Song P, Xu F, Xu L, Shao F, Guo M, Huang W, Kong L, Wu X, Xu Q. cis- Khellactone Inhibited the Proinflammatory Macrophages via Promoting Autophagy to Ameliorate Imiquimod-Induced Psoriasis. J Invest Dermatol. 2019 Sep;139(9):1946-1956.e3. doi: 10.1016/j.jid.2019.02.021. Epub 2019 Mar 13. PMID: 30878677. 2: Olennikov DN, Fedorov IA, Kashchenko NI, Chirikova NK, Vennos C. Khellactone Derivatives and Other Phenolics of Phlojodicarpus sibiricus (Apiaceae): HPLC-DAD-ESI-QQQ-MS/MS and HPLC-UV Profile, and Antiobesity Potential of Dihydrosamidin. Molecules. 2019 Jun 19;24(12):2286. doi: 10.3390/molecules24122286. PMID: 31248222; PMCID: PMC6630902. 3: Jing W, Liu R, Du W, Luo Z, Guo P, Zhang T, Zeng A, Chang C, Fu Q. Pharmacokinetic and Metabolic Characteristics of Herb-Derived Khellactone Derivatives, A Class of Anti-HIV and Anti-Hypertensive: A Review. Molecules. 2016 Mar 8;21(3):314. doi: 10.3390/molecules21030314. PMID: 27005602; PMCID: PMC6273974. 4: Heo JH, Eom BH, Ryu HW, Kang MG, Park JE, Kim DY, Kim JH, Park D, Oh SR, Kim H. Acetylcholinesterase and butyrylcholinesterase inhibitory activities of khellactone coumarin derivatives isolated from Peucedanum japonicum Thurnberg. Sci Rep. 2020 Dec 10;10(1):21695. doi: 10.1038/s41598-020-78782-5. PMID: 33303801; PMCID: PMC7730441. 5: Kim JH, Park JH, Koo SC, Huh YC, Hur M, Park WT, Moon YH, Kim TI, Cho BO. Inhibitory Activity of Natural cis-Khellactone on Soluble Epoxide Hydrolase and Proinflammatory Cytokine Production in Lipopolysaccharides- Stimulated RAW264.7 Cells. Plants (Basel). 2023 Oct 23;12(20):3656. doi: 10.3390/plants12203656. PMID: 37896119; PMCID: PMC10610198. 6: Iwasaki D, Kanazawa M, Kawamoto F, Araho D, Murakami T, Nishizaki Y, Masumoto N, Sugimoto N. A new single-reference quantitative method using liquid chromatography with relative molar sensitivity based on 1H-qNMR for khellactone esters from Peucedanum japonicum root extract. Food Chem. 2023 Nov 30;427:136647. doi: 10.1016/j.foodchem.2023.136647. Epub 2023 Jun 26. PMID: 37379748. 7: Song PP, Wang Y, Hou YP, Mao XW, Liu ZL, Wei M, Yu JP, Wang B, Qian YY, Yan L, Xu S, Jiang YQ, Zhou DQ, Yin M, Dou J. Crucial role of Ca2+ /CN signalling pathway in the antifungal activity of disenecioyl-cis-khellactone against Botrytis cinerea. Pest Manag Sci. 2022 Nov;78(11):4649-4659. doi: 10.1002/ps.7085. Epub 2022 Aug 17. PMID: 35866518. 8: Jung S, Moon HI, Lee BS, Kim S, Quynh NTN, Yu J, Le DT, Sandag Z, Lee H, Lee H, Anh NH, Yang Y, Lim JS, Kim KI, Lee MS. Anti-cancerous effect of cis- khellactone from Angelica amurensis through the induction of three programmed cell deaths. Oncotarget. 2018 Mar 30;9(24):16744-16757. doi: 10.18632/oncotarget.24686. PMID: 29682182; PMCID: PMC5908283. 9: Park JH, Kim JH, Jang SI, Cho BO. Anti-inflammatory of disenecionyl cis-khellactone in LPS-stimulated RAW264.7 cells and the its inhibitory activity on soluble epoxide hydrolase. Heliyon. 2023 Oct 14;9(10):e21032. doi: 10.1016/j.heliyon.2023.e21032. PMID: 37876448; PMCID: PMC10590947. 10: Toropova AA, Razuvaeva YG, Olennikov DN. Dihydrosamidin: the basic khellactone ester derived from Phlojodicarpus komarovii and its impact on neurotrophic factors, energy and antioxidant metabolism after rat cerebral ischemia-reperfusion injury. Nat Prod Res. 2024 Nov 27:1-6. doi: 10.1080/14786419.2024.2433189. Epub ahead of print. PMID: 39600223. 11: Hong MJ, Kim J. Determination of the Absolute Configuration of Khellactone Esters from Peucedanum japonicum Roots. J Nat Prod. 2017 May 26;80(5):1354-1360. doi: 10.1021/acs.jnatprod.6b00947. Epub 2017 Apr 12. PMID: 28402633. 12: Seong BW, Yook CS, Chung HS, Woo WS. New cis-Khellactone Esters from Angelica flaccida. Planta Med. 1991 Oct;57(5):496-7. doi: 10.1055/s-2006-960182. PMID: 17226188. 13: Xie L, Takeuchi Y, Cosentino LM, McPhail AT, Lee KH. Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone analogues. J Med Chem. 2001 Mar 1;44(5):664-71. doi: 10.1021/jm000070g. PMID: 11262077. 14: Xie L, Takeuchi Y, Cosentino LM, Lee KH. Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents. J Med Chem. 1999 Jul 15;42(14):2662-72. doi: 10.1021/jm9900624. PMID: 10411486. 15: Song Y, Jing W, Yang F, Shi Z, Yao M, Yan R, Wang Y. Simultaneously enantiospecific determination of (+)-trans-khellactone, (+/-)-praeruptorin A, (+/-)-praeruptorin B, (+)-praeruptorin E, and their metabolites, (+/-)-cis- khellactone, in rat plasma using online solid phase extraction-chiral LC-MS/MS. J Pharm Biomed Anal. 2014 Jan;88:269-77. doi: 10.1016/j.jpba.2013.08.042. Epub 2013 Sep 7. PMID: 24095802. 16: Ren L, Du X, Hu M, Yan C, Liang T, Li Q. Design, synthesis and antitumor activity of novel 4-methyl-(3'S,4'S)-cis-khellactone derivatives. Molecules. 2013 Apr 8;18(4):4158-69. doi: 10.3390/molecules18044158. PMID: 23567363; PMCID: PMC6270253. 17: Nicolaides DN, Gautam DR, Litinas KE, Hadjipavlou-Litina DJ, Fylaktakidou KC. Synthesis and evaluation of the antioxidant and antiinflammatory activities of some benzo[l]khellactone derivatives and analogues. Eur J Med Chem. 2004 Apr;39(4):323-32. doi: 10.1016/j.ejmech.2004.01.003. PMID: 15072841. 18: Jung S, Li C, Lee S, Ohk J, Kim SK, Lee MS, Moon HI. Inhibitory effect and mechanism on antiproliferation of khellactone derivatives from herbal suitable for medical or food uses. Food Chem Toxicol. 2012 Mar;50(3-4):648-52. doi: 10.1016/j.fct.2011.11.007. Epub 2011 Nov 15. PMID: 22107989. 19: Xie L, Yu D, Wild C, Allaway G, Turpin J, Smith PC, Lee KH. Anti-AIDS agents. 52. Synthesis and anti-HIV activity of hydroxymethyl (3'R,4'R)-3',4'-di-O-(S)-camphanoyl-(+)-cis-khellactone derivatives. J Med Chem. 2004 Jan 29;47(3):756-60. doi: 10.1021/jm030416y. PMID: 14736256. 20: Chen J, Liu J, Cui D, Yan C, Meng L, Sun L, Ban S, Ge R, Liang T, Li Q. Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl- substituted (3'S,4'S)-(-)-cis-khellactone derivatives that induce apoptosis via the intrinsic pathway. Drug Des Devel Ther. 2017 Jun 23;11:1891-1904. doi: 10.2147/DDDT.S131753. PMID: 28694689; PMCID: PMC5491701.