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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O2
Molecular Weight 164.2011
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-(P-HYDROXYPHENYL)-2-BUTANONE

SMILES

CC(=O)CCC1=CC=C(O)C=C1

InChI

InChIKey=NJGBTKGETPDVIK-UHFFFAOYSA-N
InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3

HIDE SMILES / InChI

Molecular Formula C10H12O2
Molecular Weight 164.2011
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Raspberry ketone (4-(4-hydroxyphenyl) butan-2-one; RK) is a major aromatic compound of red raspberry (Rubus idaeus) and is marketed on the Internet as a food supplement. The FDA classified it as GRAS (Generally Recognized as safe) food additives during the 1960s. The structure of RK is similar to the structures of capsaicin and synephrine, compounds known to exert anti-obese actions and alter the lipid metabolism. It was shown, that RK also decreased the weights and hepatic triacylglycerol content in rodents after they had been increased by a high-fat diet. Recently was discovered, that RK may exert anti-adipogenic effects through modulation of the HO-1/Wnt/beta-catenin signaling pathway. Investigations of raspberry ketone in quantitative structure-activity relationship (QSAR) models indicated potential cardiotoxic effects and potential effects on reproduction/development. Taking into account the high intake via supplements, the compound's toxic potential should be clarified with further experimental studies. In UK the pure compound is regarded as novel food requiring authorisation prior to marketing but raspberry ketone is not withdrawn from Internet sites from this country.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dosage of Raspberry Ketone to take is 100 mg, taken once per day, especially for first time users of the supplement. However, is possible to intake to about 2 or 3 100 mg capsule of the supplement per day.
Route of Administration: Oral
In Vitro Use Guide
To elucidate a possible mechanism for the antiobesity action of Raspberry ketone (4-(p-hydroxyphenyl)-2-butanone/RK), its effects on the expression and the secretion of adiponectin, lipolysis, and fatty acid oxidation in 3T3-L1 were investigated. Treatment with 10 µM of RK increased lipolysis significantly in differentiated 3T3-L1 cells. An immunoassay showed that RK increased both the expression and the secretion of adiponectin, an adipocytokine mainly expressed and secreted by adipose tissue. In addition, treatment with 10 µM of RK increased the fatty acid oxidation and suppressed lipid accumulation in 3T3-L1 adipocytes.
Substance Class Chemical
Record UNII
7QY1MH15BG
Record Status Validated (UNII)
Record Version