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MedKoo Cat#: 584340 | Name: Curcumenol
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Description:

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

Curcumenol is a sesquiterpene isolated from Curcuma zedoaria is known to possess a variety of health and medicinal values which includes neuroprotection, anti-inflammatory, anti-tumor and hepatoprotective activities.

Chemical Structure

Curcumenol
Curcumenol
CAS#19431-84-6

Theoretical Analysis

MedKoo Cat#: 584340

Name: Curcumenol

CAS#: 19431-84-6

Chemical Formula: C15H22O2

Exact Mass: 234.1620

Molecular Weight: 234.34

Elemental Analysis: C, 76.88; H, 9.46; O, 13.65

Price and Availability

Size Price Availability Quantity
5mg USD 300.00 2 Weeks
10mg USD 500.00 2 Weeks
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Related CAS #
No Data
Synonym
Curcumenol; (+)-Curcumenol
IUPAC/Chemical Name
6H-3a,6-Epoxyazulen-6-ol, 1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-, (3S-(3-alpha,3a-alpha,6-alpha,8a-beta))-
InChi Key
ISFMXVMWEWLJGJ-NZBPQXDJSA-N
InChi Code
InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3/t11-,12-,14-,15+/m0/s1
SMILES Code
O[C@]12/C(C[C@]3(O2)[C@@H](C)CC[C@@]3([H])C(C)=C1)=C(C)/C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 234.34 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: Lo JY, Kamarudin MN, Hamdi OA, Awang K, Kadir HA. Curcumenol isolated from Curcuma zedoaria suppresses Akt-mediated NF-κB activation and p38 MAPK signaling pathway in LPS-stimulated BV-2 microglial cells. Food Funct. 2015 Nov;6(11):3550-9. doi: 10.1039/c5fo00607d. Epub 2015 Aug 24. PubMed PMID: 26301513. 2: Chen LX, Zhao Q, Zhang M, Liang YY, Ma JH, Zhang X, Ding LQ, Zhao F, Qiu F. Biotransformation of Curcumenol by Mucor polymorphosporus. J Nat Prod. 2015 Apr 24;78(4):674-80. doi: 10.1021/np500845z. Epub 2015 Mar 30. PubMed PMID: 25821895. 3: Hamdi OA, Feroz SR, Shilpi JA, Anouar el H, Mukarram AK, Mohamad SB, Tayyab S, Awang K. Spectrofluorometric and molecular docking studies on the binding of curcumenol and curcumenone to human serum albumin. Int J Mol Sci. 2015 Mar 6;16(3):5180-93. doi: 10.3390/ijms16035180. PubMed PMID: 25756376; PubMed Central PMCID: PMC4394470. 4: Ahmed Hamdi OA, Awang K, Hadi AH, Syamsir DR, Ng SW. Curcumenol from Curcuma zedoaria: a second monoclinic modification. Acta Crystallogr Sect E Struct Rep Online. 2010 Oct 20;66(Pt 11):o2844. doi: 10.1107/S1600536810040559. PubMed PMID: 21589030; PubMed Central PMCID: PMC3009189. 5: Sun DX, Fang ZZ, Zhang YY, Cao YF, Yang L, Yin J. Inhibitory effects of curcumenol on human liver cytochrome P450 enzymes. Phytother Res. 2010 Aug;24(8):1213-6. doi: 10.1002/ptr.3102. PubMed PMID: 20148399. 6: Pan W, Yang L, Feng W, Lin L, Li C, Liu W, Gan G, Fan J, Zou J, Wang Z, Pan H. Determination of five sesquiterpenoids in Xingnaojing injection by quantitative analysis of multiple components with a single marker. J Sep Sci. 2015 Oct;38(19):3313-23. doi: 10.1002/jssc.201500494. Epub 2015 Aug 27. PubMed PMID: 26200507. 7: Han XH, Ye YY, Guo BF, Liu S. [Effects of platycodin D in combination with different active ingredients of Chinese herbs on proliferation and invasion of 4T1 and MDA-MB-231 breast cancer cell lines]. Zhong Xi Yi Jie He Xue Bao. 2012 Jan;10(1):67-75. Chinese. PubMed PMID: 22237277. 8: Hikino H, Sakurai Y, Numabe S, Takemoto T. Structure of curcumenol. Chem Pharm Bull (Tokyo). 1968 Jan;16(1):39-42. PubMed PMID: 5677232. 9: Boligon AA, Schwanz TG, Piana M, Bandeira RV, Frohlich JK, de Brum TF, Zadra M, Athayde ML. Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Nat Prod Res. 2013;27(1):68-71. doi: 10.1080/14786419.2011.653971. Epub 2012 Jan 24. PubMed PMID: 22273350. 10: 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. PubMed PMID: 25126594; PubMed Central PMCID: PMC4121215. 11: Abdel-Lateef E, Mahmoud F, Hammam O, El-Ahwany E, El-Wakil E, Kandil S, Abu Taleb H, El-Sayed M, Hassenein H. Bioactive chemical constituents of Curcuma longa L. rhizomes extract inhibit the growth of human hepatoma cell line (HepG2). Acta Pharm. 2016 Sep 1;66(3):387-98. doi: 10.1515/acph-2016-0028. PubMed PMID: 27383887. 12: Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M. Medicinal foodstuffs. XXIX. Potent protective effects of sesquiterpenes and curcumin from Zedoariae Rhizoma on liver injury induced by D-galactosamine/lipopolysaccharide or tumor necrosis factor-alpha. Biol Pharm Bull. 2002 May;25(5):627-31. PubMed PMID: 12033504. 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. eCollection 2016. PubMed PMID: 27134643; PubMed Central PMCID: PMC4850745. 14: Yang FQ, Yang J, Zhang XM, Xu P, Xia ZN. Analysis of volatile components in Curcuma rhizome by microemulsion electrokinetic chromatography. J Chromatogr Sci. 2013 Feb;51(2):155-60. doi: 10.1093/chromsci/bms120. Epub 2012 Jul 23. PubMed PMID: 22824329. 15: Tanaka K, Kuba Y, Ina A, Watanabe H, Komatsu K. Prediction of cyclooxygenase inhibitory activity of curcuma rhizome from chromatograms by multivariate analysis. Chem Pharm Bull (Tokyo). 2008 Jul;56(7):936-40. PubMed PMID: 18591805. 16: Suphrom N, Pumthong G, Khorana N, Waranuch N, Limpeanchob N, Ingkaninan K. Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb. Fitoterapia. 2012 Jul;83(5):864-71. doi: 10.1016/j.fitote.2012.03.017. Epub 2012 Mar 21. PubMed PMID: 22465508. 17: Aspollah Sukari M, Wah TS, Saad SM, Rashid NY, Rahmani M, Lajis NH, Hin TY. Bioactive sesquiterpenes from Curcuma ochrorhiza and Curcuma heyneana. Nat Prod Res. 2010 May;24(9):838-45. doi: 10.1080/14786410903052951. PubMed PMID: 20461629. 18: Yang FQ, Wang HK, Chen H, Chen JD, Xia ZN. Fractionation of volatile constituents from curcuma rhizome by preparative gas chromatography. J Autom Methods Manag Chem. 2011;2011:942467. doi: 10.1155/2011/942467. Epub 2011 Aug 18. PubMed PMID: 21876660; PubMed Central PMCID: PMC3159003. 19: Navarro Dde F, de Souza MM, Neto RA, Golin V, Niero R, Yunes RA, Delle Monache F, Cechinel Filho V. Phytochemical analysis and analgesic properties of Curcuma zedoaria grown in Brazil. Phytomedicine. 2002 Jul;9(5):427-32. PubMed PMID: 12222663. 20: Yang FQ, Li SP, Chen Y, Lao SC, Wang YT, Dong TT, Tsim KW. Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):552-8. PubMed PMID: 15946818.

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