U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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UK the pure compound is regarded as novel food requiring authorisation prior to marketing but raspberry ketone is not withdrawn from Internet sites from this country.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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: HO-1/Wnt/beta-catenin signaling pathway
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay.
2010 Apr 1
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.
2011 Feb 8
Patents

Sample Use Guides

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
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.
Name Type Language
4-(P-HYDROXYPHENYL)-2-BUTANONE
FCC   FHFI  
Common Name English
4-(P-HYDROXYPHENYL)-2-BUTANONE [FCC]
Common Name English
RASPBERRY KETONE
INCI   USP-RS   VANDF  
INCI  
Official Name English
4-(P-HYDROXYPHENYL)-2-BUTANONE [FHFI]
Common Name English
RASPBERRY KETONE [VANDF]
Common Name English
4-(4-HYDROXYPHENYL)BUTAN-2-ONE
Systematic Name English
P-HYDROXY-BENZYLACETONE
Common Name English
FRAMBINONE
Common Name English
RASPBERRY KETONE [USP IMPURITY]
Common Name English
DOBUTAMINE IMPURITY B [EP IMPURITY]
Common Name English
NSC-26515
Code English
RACTOPAMINE HYDROCHLORIDE SUSPENSION IMPURITY, RASPBERRY KETONE- [USP IMPURITY]
Common Name English
P-HYDROXYBENZYL ACETONE
Common Name English
RASPBERRY KETONE [INCI]
Common Name English
4(P-HYDROXYPHENYL)-2-BUTANONE
Common Name English
2-BUTANONE, 4-(P-HYDROXYPHENYL)-
Common Name English
RASPBERRY KETONE [USP-RS]
Common Name English
FEMA NO. 2588
Code English
RHEOSMIN
Common Name English
RASPBERRY KETONE [MI]
Common Name English
2-BUTANONE, 4-(4-HYDROXYPHENYL)-
Systematic Name English
OXYPHENYLON
Common Name English
4-(4-HYDROXYPHENYL)BUTAN-2-ONE [WHO-DD]
Common Name English
DOBUTAMINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
JECFA EVALUATION 4-(P-HYDROXYPHENYL)-2-BUTANONE
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
DSLD 3353 (Number of products:284)
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
Code System Code Type Description
EVMPD
SUB61972
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
PUBCHEM
21648
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
MERCK INDEX
m11999
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
226-806-4
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
FDA UNII
7QY1MH15BG
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
RXCUI
1860422
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1598813
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
EVMPD
SUB63774
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
HSDB
8163
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
NSC
26515
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
WIKIPEDIA
RASPBERRY KETONE
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
SMS_ID
100000134384
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
DAILYMED
7QY1MH15BG
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
CHEBI
68656
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID5044495
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
CAS
5471-51-2
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY
JECFA MONOGRAPH
601
Created by admin on Fri Dec 15 16:53:10 GMT 2023 , Edited by admin on Fri Dec 15 16:53:10 GMT 2023
PRIMARY