Zederone | CAS#7727-79-9 | sesquiterpene

MedKoo Cat#: 145740 | Name: Zederone

Description:

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

Zederone is a germacrane-type sesquiterpene isolated from the rhizomes of Curcuma elata (Zingiberaceae). Zederone significantly inhibits cell proliferation and downregulates the protein expressions of mTOR and phosphorylated p70 S6 kinase (p-p70s6K) in SKOV3 cells. Zederone is a bioactive compound with notable anticancer and antibacterial properties, though its hepatotoxic potential warrants caution in its application.

Chemical Structure

Zederone

CAS#7727-79-9

Theoretical Analysis

MedKoo Cat#: 145740

Name: Zederone

CAS#: 7727-79-9

Chemical Formula: C15H18O3

Exact Mass: 246.1300

Molecular Weight: 246.31

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

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

Zederone;

IUPAC/Chemical Name

(1aR,10aR,E)-1a,5,9-trimethyl-1a,3,6,10a-tetrahydrooxireno[2',3':4,5]cyclodeca[1,2-b]furan-10(2H)-one

InChi Key

CVIVANCKIBYAOP-KOMYPQRHSA-N

InChi Code

1S/C15H18O3/c1-9-5-4-6-15(3)14(18-15)13(16)12-10(2)8-17-11(12)7-9/h5,8,14H,4,6-7H2,1-3H3/b9-5+/t14-,15+/m0/s1

SMILES Code

CC1=COC2=C1C(=O)[C@@H]3O[C@]3(C)CC\C=C(C)\C2

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 246.31 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.

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: Borah S, Sarkar P, Sharma HK. Zederone Improves the Fecal Microbial Profile in Dementia Induced Rat Model: A First Report. CNS Neurol Disord Drug Targets. 2022;21(4):335-342. doi: 10.2174/1871527320666210827114227. PMID: 34455974. 2: Pimkaew P, Suksen K, Somkid K, Chokchaisiri R, Jariyawat S, Chuncharunee A, Suksamrarn A, Piyachaturawat P. Zederone, a sesquiterpene from Curcuma elata Roxb, is hepatotoxic in mice. Int J Toxicol. 2013 Nov-Dec;32(6):454-62. doi: 10.1177/1091581813504595. Epub 2013 Sep 30. PMID: 24082031. 3: Hikino H, Takahashi S, Sakurai Y, Takemoto T, Bhacca NS. Structure of zederone. Chem Pharm Bull (Tokyo). 1968 Jun;16(6):1081-7. doi: 10.1248/cpb.16.1081. PMID: 5706816. 4: Zhang Z, Li L, Wang J, Liang X, Wang Y, Wang X, Qiao Y, Zhao B. A study of zederone for the inhibition on ovarian cancer cell proliferation through mTOR/p70s6K signalling pathway. J BUON. 2020 Mar-Apr;25(2):785-791. PMID: 32521868. 5: Pimkaew P, Küblbeck J, Petsalo A, Jukka J, Suksamrarn A, Juvonen R, Auriola S, Piyachaturawat P, Honkakoski P. Interactions of sesquiterpenes zederone and germacrone with the human cytochrome P450 system. Toxicol In Vitro. 2013 Sep;27(6):2005-12. doi: 10.1016/j.tiv.2013.07.004. Epub 2013 Jul 12. PMID: 23850985. 6: Zárybnický T, Boušová I, Ambrož M, Skálová L. Hepatotoxicity of monoterpenes and sesquiterpenes. Arch Toxicol. 2018 Jan;92(1):1-13. doi: 10.1007/s00204-017-2062-2. Epub 2017 Sep 13. PMID: 28905185. 7: Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriyadacha Y, Wu L, Yoshikawa M. Sesquiterpenes from Curcuma comosa. J Nat Med. 2009 Jan;63(1):102-4. doi: 10.1007/s11418-008-0282-8. Epub 2008 Jul 29. PMID: 18663560. 8: Faiz Hossain C, Al-Amin M, Rahman KM, Sarker A, Alam MM, Chowdhury MH, Khan SN, Sultana GN. Analgesic principle from Curcuma amada. J Ethnopharmacol. 2015 Apr 2;163:273-7. doi: 10.1016/j.jep.2015.01.018. Epub 2015 Jan 28. PMID: 25636664. 9: Burapan S, Kim M, Paisooksantivatana Y, Eser BE, Han J. Thai Curcuma Species: Antioxidant and Bioactive Compounds. Foods. 2020 Sep 2;9(9):1219. doi: 10.3390/foods9091219. PMID: 32887356; PMCID: PMC7555267. 10: Zheng W, Zhou H, Fu Z, Feng L, Wen D, Liang X, Cao L. Integration of 16 S rRNA gene sequencing, metabonomics and metagenome analysis to investigate the mechanism of Sparganium stoloniferum-Curcuma phaeocaulis in treating of endometriosis in rats. J Pharm Biomed Anal. 2024 Apr 15;241:115970. doi: 10.1016/j.jpba.2024.115970. Epub 2024 Jan 17. PMID: 38277707. 11: Zhou CX, Zhang LS, Chen FF, Wu HS, Mo JX, Gan LS. Terpenoids from Curcuma wenyujin increased glucose consumption on HepG2 cells. Fitoterapia. 2017 Sep;121:141-145. doi: 10.1016/j.fitote.2017.06.011. Epub 2017 Jun 15. PMID: 28625730. 12: Makabe H, Maru N, Kuwabara A, Kamo T, Hirota M. Anti-inflammatory sesquiterpenes from Curcuma zedoaria. Nat Prod Res. 2006 Jun;20(7):680-5. doi: 10.1080/14786410500462900. PMID: 16901812. 13: Liu F, Bai X, Yang FQ, Zhang XJ, Hu Y, Li P, Wan JB. Discriminating from species of Curcumae Radix (Yujin) by a UHPLC/Q-TOFMS-based metabolomics approach. Chin Med. 2016 Apr 29;11:21. doi: 10.1186/s13020-016-0095-8. PMID: 27134643; PMCID: PMC4850745. 14: Wang LJ, Xiong J, Liu ST, Liu XH, Hu JF. Sesquiterpenoids from Chloranthus henryi and their anti-neuroinflammatory activities. Chem Biodivers. 2014 Jun;11(6):919-28. doi: 10.1002/cbdv.201300283. PMID: 24934677. 15: Xie M, Zhang M, Qiao Y, Yang Y, Xie F, Chen L, Liu N, Gu J. Molecular mechanism of PSORI-CM01 for psoriasis by regulating the inflammatory cytokines network. J Ethnopharmacol. 2024 Jan 10;318(Pt A):116935. doi: 10.1016/j.jep.2023.116935. Epub 2023 Jul 20. PMID: 37479070. 16: Ren X, He T, Wang J, Wang L, Wang Y, Liu X, Dong Y, Ma J, Jia J, Song R, Fan Q, Wei J, Yu A, Wang X, She G. UV spectroscopy and HPLC combined with chemometrics for rapid discrimination and quantification of Curcumae Rhizoma from three botanical origins. J Pharm Biomed Anal. 2021 Aug 5;202:114145. doi: 10.1016/j.jpba.2021.114145. Epub 2021 May 21. PMID: 34051484. 17: Wachananawat B, Kong BL, Shaw PC, Bongcheewin B, Sangvirotjanapat S, Prombutara P, Pornputtapong N, Sukrong S. Characterization and phylogenetic analysis of the complete chloroplast genome of Curcuma comosa and C. latifolia. Heliyon. 2024 May 15;10(10):e31248. doi: 10.1016/j.heliyon.2024.e31248. PMID: 38813184; PMCID: PMC11133819. 18: Ahmed Hamdi OA, Syed Abdul Rahman SN, Awang K, Abdul Wahab N, Looi CY, Thomas NF, Abd Malek SN. Cytotoxic constituents from the rhizomes of Curcuma zedoaria. ScientificWorldJournal. 2014;2014:321943. doi: 10.1155/2014/321943. Epub 2014 Jul 13. PMID: 25126594; PMCID: PMC4121215. 19: Qin Y, Fei C, Zhang W, Su L, Ji D, Bian Z, Wang M, Li Y, Mao C, Zhao X, Lu T. Based on UPLC/MS/MS and Bioinformatics Analysis to Explore the Difference Substances and Mechanism of Curcumae Radix (Curcuma wenyujin) in Dysmenorrhea. Chem Biodivers. 2022 Oct;19(10):e202200361. doi: 10.1002/cbdv.202200361. Epub 2022 Sep 16. PMID: 36017755. 20: Al-Amin M, Eltayeb NM, Hossain CF, Rahiman SSF, Khairuddean M, Muhamad Salhimi S. Bioactive compounds from Curcuma aeruginosa and the effect of comosone II on the migration and invasion of breast cancer cells. J Asian Nat Prod Res. 2022 Jun 4:1-12. doi: 10.1080/10286020.2022.2081562. Epub ahead of print. PMID: 35658750.