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MedKoo Cat#: 464188 | Name: Octahydrocurcumin
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Description:

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

Octahydrocurcumin is an active metabolite of curcumin that has diverse biological activities. Octahydrocurcumin 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.

Chemical Structure

Octahydrocurcumin
Octahydrocurcumin
CAS#36062-07-4

Theoretical Analysis

MedKoo Cat#: 464188

Name: Octahydrocurcumin

CAS#: 36062-07-4

Chemical Formula: C21H28O6

Exact Mass: 376.1886

Molecular Weight: 376.45

Elemental Analysis: C, 67.00; H, 7.50; O, 25.50

Price and Availability

Size Price Availability Quantity
1mg USD 410.00 2 Weeks
5mg USD 600.00 2 Weeks
10mg USD 840.00 2 Weeks
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Related CAS #
No Data
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Octahydrocurcumin is a hydrogenated derivatives of curcumin; metabolite of curcumin.
In vitro activity:
The current investigation designed an efficient synthesis method to produce OHC (octahydrocurcumin), and comparatively explored the anti-cancer effect and potential mechanism of OHC and CUR in an H22 ascites tumor-bearing mice model. The results indicated that OHC had a relatively wide margin of safety, and exhibited superior effects to CUR in suppressing the tumor growth, including ascending weight, abdominal circumference, ascites volume and cancer cell viability. OHC significantly induced H22 cell apoptosis by upregulating the p53 expression and downregulating the MDM2 expression. OHC also remarkably decreased the Bcl-2 and Bcl-xl protein expressions, and increased the Bax and Bad expressions in ascitic cells. Reference: Food Funct. 2018 Apr 25;9(4):2005-2014. https://pubmed.ncbi.nlm.nih.gov/29616245/
In vivo activity:
The current investigation designed an efficient synthesis method to produce OHC (octahydrocurcumin), and comparatively explored the anti-cancer effect and potential mechanism of OHC and CUR in an H22 ascites tumor-bearing mice model. The results indicated that OHC had a relatively wide margin of safety, and exhibited superior effects to CUR in suppressing the tumor growth, including ascending weight, abdominal circumference, ascites volume and cancer cell viability. OHC significantly induced H22 cell apoptosis by upregulating the p53 expression and downregulating the MDM2 expression. OHC also remarkably decreased the Bcl-2 and Bcl-xl protein expressions, and increased the Bax and Bad expressions in ascitic cells. Reference: Food Funct. 2018 Apr 25;9(4):2005-2014. https://pubmed.ncbi.nlm.nih.gov/29616245/
Solvent mg/mL mM
Solubility
DMSO 100.0 265.64
Ethanol 10.0 26.56
Methanol 10.0 26.56
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

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
Formulation protocol:
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.
In vitro protocol:
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.
In vivo protocol:
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.
1: 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. 2: Guo Q, Li W, Wang R, Li J, Zhang R, Zhang X, Wang Z. Screening of activators of 2,3-diphosphoglycerate mutase from traditional Chinese herb medicines. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2022 Aug 1;51(4):430-437. English. doi: 10.3724/zdxbyxb-2022-0178. PMID: 37202106; PMCID: PMC10264992. 3: Qiao X, Ye L, Lu J, Pan C, Fei Q, Zhu Y, Li H, Lin H, Ge RS, Wang Y. Curcumin analogues exert potent inhibition on human and rat gonadal 3β-hydroxysteroid dehydrogenases as potential therapeutic agents: structure-activity relationship and in silico docking. J Enzyme Inhib Med Chem. 2023 Dec;38(1):2205052. doi: 10.1080/14756366.2023.2205052. PMID: 37184069; PMCID: PMC10187107. 4: Luo D, Lin Y, Chen J, Huang X, Xie Y, Liu Y, Ni S, Su Z, Li Y, Zhang Z. Stereoisomers of octahydrocurcumin, the hydrogenated metabolites of curcumin, display stereoselective activity on the CYP2E1 enzyme in L-02 cells. Food Funct. 2023 Mar 20;14(6):2822-2835. doi: 10.1039/d2fo03892g. PMID: 36866793. 5: Sang J, Chu J, Zhao X, Quan H, Ji Z, Wang S, Tang Y, Hu Z, Li H, Li L, Ge RS. Curcuminoids inhibit human and rat placental 3β-hydroxysteroid dehydrogenases: Structure-activity relationship and in silico docking analysis. J Ethnopharmacol. 2023 Apr 6;305:116051. doi: 10.1016/j.jep.2022.116051. Epub 2022 Dec 23. PMID: 36572324. 6: Niwa T, Kato Y, Osawa T. Chemical and in vitro biological formation of octahydrocurcumin stereoisomers, and in vitro activity of raceme and meso- octahydrocurcumin. Biosci Biotechnol Biochem. 2023 Feb 24;87(3):303-307. doi: 10.1093/bbb/zbac204. PMID: 36520062. 7: Puente AR, Nagabhushanam K, Ganjihal S, Majeed M, Polavarapu PL. Chiroptical spectroscopic studies for the absolute configuration determination of hexahydrocurcumin and octahydrocurcumin. Chirality. 2022 Dec;34(12):1515-1525. doi: 10.1002/chir.23511. Epub 2022 Oct 27. PMID: 36300855. 8: Niwa T, Yokoyama SI, Mochizuki M, Osawa T. In Vitro Production of Optically Active Octahydrocurcumin by Human Intestinal Bacterium. Biol Pharm Bull. 2022;45(3):378-381. doi: 10.1248/bpb.b21-00992. PMID: 35228404. 9: 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. 10: 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. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: 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. 17: 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. 18: 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. 19: 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. 20: 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.

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WF 3681

WF 3681

ITV-8912

ITV-8912

JWH-091

JWH-091