WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H464188
CAS#: 36062-07-4
Description: Octahydrocurcumin is an active metabolite of curcumin that has diverse biological activities. It scavenges DPPH radicals in a cell-free assay (IC50 = 12.3 µM). Octahydrocurcumin (6.25 µM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 levels, production of nitric oxide (NO), and nuclear translocation of NF-ᴋB in RAW 264.7 cells. It is active against the bacteria B. subtilis, K. pneumoniae, E. coli, E. aerogenes, P. aeruginosa, and S. aureus, as well as C. albicans and the plant pathogenic fungus A. niger, in disc assays. Octahydrocurcumin (5, 10, and 20 mg/kg) increases survival, reduces tumor weight, and induces tumor cell apoptosis in an H22 murine hepatocellular carcinoma model.
Hodoodo Cat#: H464188
Name: Octahydrocurcumin
CAS#: 36062-07-4
Chemical Formula: C21H28O6
Exact Mass: 376.19
Molecular Weight: 376.449
Elemental Analysis: C, 67.00; H, 7.50; O, 25.50
Synonym: Octahydrocurcumin; Hexahydrobisdemethoxycurcumin; Hexahydrocurcuminol;
IUPAC/Chemical Name: 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol
InChi Key: OELMAFBLFOKZJD-UHFFFAOYSA-N
InChi Code: InChI=1S/C21H28O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,16-17,22-25H,3-4,7-8,13H2,1-2H3
SMILES Code: OC1=C(C=C(C=C1)CCC(CC(CCC2=CC(OC)=C(C=C2)O)O)O)OC
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: 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| To be determined | 0.0 | 100.00 |
The following data is based on the product molecular weight 376.45 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: Xie QF, Cheng JJ, Chen JF, Feng YC, Lin GS, Xu Y. Comparation of Anti- Inflammatory and Antioxidantactivities of Curcumin, Tetrahydrocurcuminand Octahydrocurcuminin LPS-Stimulated RAW264.7 Macrophages. Evid Based Complement Alternat Med. 2020 Dec 22;2020:8856135. doi: 10.1155/2020/8856135. PMID: 33424997; PMCID: PMC7772021.
2: Pandey A, Chaturvedi M, Mishra S, Kumar P, Somvanshi P, Chaturvedi R. Reductive metabolites of curcumin and their therapeutic effects. Heliyon. 2020 Nov 12;6(11):e05469. doi: 10.1016/j.heliyon.2020.e05469. PMID: 33241148; PMCID: PMC7674297.
3: Trivedi MK, Panda P, Sethi KK, Gangwar M, Mondal SC, Jana S. Solid and liquid state characterization of tetrahydrocurcumin using XRPD, FT-IR, DSC, TGA, LC-MS, GC-MS, and NMR and its biological activities. J Pharm Anal. 2020 Aug;10(4):334-345. doi: 10.1016/j.jpha.2020.02.005. Epub 2020 Feb 15. PMID: 32923007; PMCID: PMC7474126.
4: Li P, Ding L, Cao S, Feng X, Zhang Q, Chen Y, Zhang N, Qiu F. Curcumin metabolites contribute to the effect of curcumin on ameliorating insulin sensitivity in high-glucose-induced insulin-resistant HepG2 cells. J Ethnopharmacol. 2020 Sep 15;259:113015. doi: 10.1016/j.jep.2020.113015. Epub 2020 May 25. PMID: 32464315.
5: Luo DD, Chen JF, Liu JJ, Xie JH, Zhang ZB, Gu JY, Zhuo JY, Huang S, Su ZR, Sun ZH. Tetrahydrocurcumin and octahydrocurcumin, the primary and final hydrogenated metabolites of curcumin, possess superior hepatic-protective effect against acetaminophen-induced liver injury: Role of CYP2E1 and Keap1-Nrf2 pathway. Food Chem Toxicol. 2019 Jan;123:349-362. doi: 10.1016/j.fct.2018.11.012. Epub 2018 Nov 10. PMID: 30423402.
6: Zhang ZB, Luo DD, Xie JH, Xian YF, Lai ZQ, Liu YH, Liu WH, Chen JN, Lai XP, Lin ZX, Su ZR. Curcumin's Metabolites, Tetrahydrocurcumin and Octahydrocurcumin, Possess Superior Anti-inflammatory Effects in vivo Through Suppression of TAK1-NF-κB Pathway. Front Pharmacol. 2018 Oct 17;9:1181. doi: 10.3389/fphar.2018.01181. PMID: 30386242; PMCID: PMC6199526.
7: Jude S, Amalraj A, Kunnumakkara AB, Divya C, Löffler BM, Gopi S. Development of Validated Methods and Quantification of Curcuminoids and Curcumin Metabolites and Their Pharmacokinetic Study of Oral Administration of Complete Natural Turmeric Formulation (Cureit™) in Human Plasma via UPLC/ESI-Q-TOF-MS Spectrometry. Molecules. 2018 Sep 20;23(10):2415. doi: 10.3390/molecules23102415. PMID: 30241377; PMCID: PMC6222699.
8: Zhang Z , Luo D , Xie J , Lin G , Zhou J , Liu W , Li H , Yi T , Su Z , Chen J . Octahydrocurcumin, a final hydrogenated metabolite of curcumin, possesses superior anti-tumor activity through induction of cellular apoptosis. Food Funct. 2018 Apr 25;9(4):2005-2014. doi: 10.1039/c7fo02048a. PMID: 29616245.
9: Morales NP, Sirijaroonwong S, Yamanont P, Phisalaphong C. Electron Paramagnetic Resonance Study of the Free Radical Scavenging Capacity of Curcumin and Its Demethoxy and Hydrogenated Derivatives. Biol Pharm Bull. 2015;38(10):1478-83. doi: 10.1248/bpb.b15-00209. PMID: 26424013.
10: Zhao F, Gong Y, Hu Y, Lu M, Wang J, Dong J, Chen D, Chen L, Fu F, Qiu F. Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: translocation of nuclear factor-κB as potential target. Mol Med Rep. 2015 Apr;11(4):3087-93. doi: 10.3892/mmr.2014.3079. Epub 2014 Dec 11. PMID: 25502175.
11: Maehara S, Ikeda M, Haraguchi H, Kitamura C, Nagoe T, Ohashi K, Shibuya H. Microbial conversion of curcumin into colorless hydroderivatives by the endophytic fungus Diaporthe sp. associated with Curcuma longa. Chem Pharm Bull (Tokyo). 2011;59(8):1042-4. doi: 10.1248/cpb.59.1042. PMID: 21804251.
12: Deters M, Knochenwefel H, Lindhorst D, Koal T, Meyer HH, Hänsel W, Resch K, Kaever V. Different curcuminoids inhibit T-lymphocyte proliferation independently of their radical scavenging activities. Pharm Res. 2008 Aug;25(8):1822-7. doi: 10.1007/s11095-008-9579-2. Epub 2008 Apr 22. PMID: 18427962.
13: Somparn P, Phisalaphong C, Nakornchai S, Unchern S, Morales NP. Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biol Pharm Bull. 2007 Jan;30(1):74-8. doi: 10.1248/bpb.30.74. PMID: 17202663.
14: Pan MH, Lin-Shiau SY, Lin JK. Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down- regulation of IkappaB kinase and NFkappaB activation in macrophages. Biochem Pharmacol. 2000 Dec 1;60(11):1665-76. doi: 10.1016/s0006-2952(00)00489-5. PMID: 11077049.
