Hexahydrocurcumin - ≥99% , CAS No.36062-05-2

CAS: 36062-05-2 Cat. No.: H351682 Molecular Weight: 374.43

GRADE & PURITY ≥99%

Synonyms

5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone | 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Hexahydrocurcumin is one of the major metabolites of curcumin and a selective, orally active COX-2 inhibitor. Hexahydrocurcumin is inactive against COX-1. Hexahydrocurcumin has antioxidant, anticancer and anti-inflammatory activities.

Specifications

Synonyms

5-hydroxy-1, 7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone | 5-hydroxy-1, 7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: COC1=C(C=CC(=C1)CCC(CC(=O)CCC2=CC(=C(C=C2)O)OC)O)O
• IUPAC Name: 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one
• InChIKey: RSAHICAPUYTWHW-UHFFFAOYSA-N
• INCHI: 1S/C21H26O6/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/h5-6,9-12,16,22,24-25H,3-4,7-8,13H2,1-2H3
• Isomeric SMILES: COC1=C(C=CC(=C1)CCC(CC(=O)CCC2=CC(=C(C=C2)O)OC)O)O
• Molecular Weight: 374.43
• Reaxy-Rn: 2486876
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2486876&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Diarylheptanoids
      • Subclass Linear diarylheptanoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Diarylheptanoids
• Subclass: Linear diarylheptanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Curcuminoids
• Alternative Parents: Gingerols Fatty alcohols Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Beta-hydroxy ketones Secondary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Curcumin - Gingerol - Methoxyphenol - Fatty alcohol - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Beta-hydroxy ketone - Fatty acyl - Benzenoid - Ketone - Secondary alcohol - Ether - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
• External Descriptors: diarylheptanoid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

DNMT1 Tclin DNA (cytosine-5)-methyltransferase 1 (978 Activities)

Discover Target: DNMT1

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BACE1 Tchem Beta-secretase 1 (15641 Activities)

Discover Target: BACE1

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HEK293 (82097 Activities)

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Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Leishmania major (2877 Activities)

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Leishmania mexicana (936 Activities)

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RAW264.7 (28094 Activities)

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RBL-2H3 (1162 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO: 45 mg/mL (120.19 mM), Need ultrasonic
• Molecular Weight: 374.400 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 374.173 Da
• Monoisotopic Mass: 374.173 Da
• Topological Polar Surface Area: 96.200 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 442.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Dan Yuan, Qi Li, Qibo Zhang, Feibai Zhou, Qiangzhong Zhao, Mouming Zhao.  (2023)  Enhanced curcumin transportation across epithelial barrier by mucus-permeable soy protein nanoparticles-mediated dual transcytosis pathways.  FOOD CHEMISTRY,      [PMID:37897825] [10.1016/j.foodchem.2023.137771]

2. Jiaying Hao, Yunju Zhang, Kaiwei Liu, Boyu Zhang, Hao Wang, Yuning Jin, Bin Wang, Di Wang, Ying Li, Xueli Wei, Qinyuan Ma, Xiuzhen Gao.  (2025)  Structure-Guided Evolution of Curcumin Reductase for Sustainable Tetrahydrocurcumin Biosynthesis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41026119] [10.1021/acs.jafc.5c07455]