Hexahydrocurcumin
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Grundinformationen
- CAS
36062-05-2- Standard-SMILES
COc1cc(CCC(=O)CC(O)CCc2ccc(O)c(OC)c2)ccc1O- InChIKey
RSAHICAPUYTWHW-UHFFFAOYSA-N- Summenformel
- C21H26O6
- Durchschnittliche Molmasse
- 374,433 g/mol
- Monoisotopische Masse
- 374,17293855
Namen und Bezeichner
- Bevorzugter Name
- Hexahydrocurcumin
- IUPAC
- 5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one
- Englischer Name
- Hexahydrocurcumin
- Summenformel
- C21H26O6
- Molmasse
- 374.43
Namen und Synonyme
5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanoneHexahydrocurcuminHexahydrocurcumin-RMHexahydrocurcumin, BR5-dimethyl ether Gallic AcidHexahydrocurcumin, 10 mM in DMSO5-dimethoxy-4-hydroxy Benzoic Acid1,7-Bis(4-hydroxy-3-methoxyphenyl)-5-hydroxyheptan-3-one1,7-Bis(3-methoxy-4-hydroxyphenyl)-5-hydroxy-3-heptanone5-Hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one
Datenbank-Bezeichner
- CAS
36062-05-2- PubChem CID
- 5318039
- DTXSID
DTXSID00415731- ChEMBL
CHEMBL479650- ChEBI
CHEBI:81358- UNII
- RNL5XJ2BA7
- EC Number
- 924-435-9
- Nikkaji
- J445.265H
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 80 · 80-82℃
- Siedepunkt
- 622.6 · 622.6±55.0 °C(Predicted)
- Dichte
- 1.226 · 1.226
- Flammpunkt
- 218 ℃ · 218℃
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform (Sparingly), Ethyl Acetate (Slightly), DCM, DMSO
- Aggregatzustand
- Solid
- pka
- 10.02 · 10.02±0.20(Predicted)
- Farbe
- Pale Yellow
- BRN
- 2486876 · 2486876
- Major Application
- food and beverages
- 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
- InChIKey
- RSAHICAPUYTWHW-UHFFFAOYSA-N
- SMILES
- O=C(CC(O)CCC1=CC(OC)=C(O)C=C1)CCC2=CC(OC)=C(O)C=C2
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungHexahydrocurcumin is a natural product and glucuronide metabolite of curcumin that has anti-inflammatory, antioxidant, and anticancer properties. It reduces prostaglandin E2 (PGE2) production stimulated by phorbol 12-myristate 13-acetate (PMA; ) by 37% in human colonic epithelial cells when used at a concentration of 20 μM. Hexahydrocurcumin (3.125-25 μM) inhibits overproduction of nitric oxide induced by LPS in RAW 264.7 macrophage cells in a concentration-dependent manner. It does not affect LPS-induced cytokine release but inhibits LPS-induced iNOS and COX-2 upregulation and NF-κB activation when used at a concentration of 50 μM. Hexahydrocurcumin prevents the formation of aberrant crypt foci in a dimethylhydrazine rat model of colon cancer and potentiates the effect of 5-fluorouracil .
VerwendenHexahydrocurcumin is an intermediate in the synthesis of Gingerenone A (G387500) which is an antifungal and antiparasitic diarylheptenone that is isolated from Zingiber officinale (more commonly known as ginger), a medicinal plant that is used to treat inflammation and musculoskeletal disorders.
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