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5471-51-2

Basic Information
CAS No.: 5471-51-2
Name: Raspberry ketone
Article Data: 75
Molecular Structure:
Molecular Structure of 5471-51-2 (Raspberry ketone)
Formula: C10H12O2
Molecular Weight: 164.204
Synonyms: 2-Butanone,4-(p-hydroxyphenyl)- (6CI,7CI,8CI);(4-Hydroxybenzyl)acetone;(p-Hydroxybenzyl)acetone;1-(4-Hydroxyphenyl)-3-butanone;1-(p-Hydroxyphenyl)-3-butanone;4-(3-Oxobutyl)phenol;4-(p-Hydroxyphenyl)-2-butanone;Frambinone;NSC 26515;Oxyphenylon;Raspberryketone;Rheosmin;4-(4-Hydroxyphenyl)-2-butanone;
EINECS: 226-806-4
Density: 1.088 g/cm3
Melting Point: 81-85 °C(lit.)
Boiling Point: 292.2 °C at 760 mmHg
Flash Point: 122.9 °C
Solubility: Insoluble in water; Soluble in ethanol and diethyl ether
Appearance: white to slightly yellow powder or needles
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22
Safety: 26-36/37/39
PSA: 37.30000
LogP: 1.91380
Synthetic route
22214-30-8, 59417-71-9, 3160-35-8

4-(4'-hydroxyphenyl)but-3-en-2-one

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 20℃; for 24h;99%
With 1 wt.% La2O3 supported titania at 200℃; for 3h; Reagent/catalyst; Temperature; Autoclave;96%
With N-benzylammonium trifluoroacetate; 1,4-dihydro-2,6-dimethyl-3,5-bis<(methylamino)carbonyl>pyridine In tetrahydrofuran at 70℃; for 16h; Sealed tube;96%
22214-30-8

(E)-4-(4-hydroxyphenyl)-3-buten-2-one

A

69617-84-1

rac-rhododendrol

B

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen In methanol at 0 - 30℃; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Time; Reflux; Inert atmosphere;A 1%
B 98%
With sodium tetrahydroborate; nickel dichloride In methanolA 38%
B 61%
With methanol; formic acid; water; silica gel; palladium dichloride for 12h; Heating;A 25%
B 45%
With baker's yeast; ethanol; D-glucose; water at 36℃; for 92h; Product distribution; var. reducing agents, also labelled;
With formic acid; palladium 10% on activated carbon; ammonium formate In methanol at 50℃; for 15h;

4-(4-((tert-butyldimethylsilyl)oxy)phenyl)butan-2-one

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;95%
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;95%
1445875-25-1

4-(4-((triisopropylsilyl)oxy)phenyl)butan-2-one

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;95%
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;75%
104-20-1

4-(4-methoxyphenyl)-2-butanone

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry;94%
With hydrogen bromide; acetic acid In water at 130℃; for 4h; Reagent/catalyst; Temperature; Solvent;86%
With hydrogen bromide; acetic acid
78-94-4

methyl vinyl ketone

108-95-2

phenol

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With 4H2O4S*C18H40N4O12S4 at 40℃; for 8h; Temperature;94%
With amberlyst-15 In toluene at 20 - 40℃;58.1%
With 1-butyl-3-methylimidazolium hydrogen sulfate at 20℃; for 24h; Friedel-Crafts Alkylation; regioselective reaction;51%

1-(4-tert.-butoxy-phenyl)-butan-3-one

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
In sulfuric acid93%
74432-58-9

4-(4-(benzyloxy)phenyl)butan-2-one

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 18 - 22℃; for 24h;93%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; for 120h; Inert atmosphere;93%

Na(1+)*C10H11O2(1-)

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With hydrogenchloride In water Industrial scale;93%
52252-58-1

2-(4-Hydroxybenzyl)acetessigsaeure-ethylester

5471-51-2

4-(4-hydroxyphenyl)-2-oxobutane

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 80℃; for 3h; Solvent; Reagent/catalyst;90%
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Chemistry

IUPAC Name: 4-(4-Hydroxyphenyl)butan-2-one
Molecular Formula: C10H12O2
Molecular Weight: 164.2 g/mol
EINECS: 226-806-4 
Density: 1.088 g/cm3
Melting Point: 81-85 °C
Boiling Point: 200 °C
Flash Point: 122.9 °C
Appearance: white powder
Index of Refraction: 1.535
Molar Refractivity: 46.97 cm3
Molar Volume: 150.8 cm3
Surface Tension: 41.8 dyne/cm
XLogP3-AA: 1.5
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 3
Tautomer Count: 6
Exact Mass: 164.08373
MonoIsotopic Mass: 164.08373
Topological Polar Surface Area: 37.3
Heavy Atom Count: 12 
Canonical SMILES: CC(=O)CCC1=CC=C(C=C1)O
InChI: InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
InChIKey: NJGBTKGETPDVIK-UHFFFAOYSA-N
EINECS: 226-806-4
Product Categories: Food and Feed Additive;Aromatic Ketones (substituted)
Molecule structure of Raspberry ketone (CAS NO.5471-51-2):

Uses

 Raspberry ketone (CAS NO.5471-51-2) is the primary aroma compound of red raspberries. It is used in perfumery, in cosmetics, and as a food additive to impart a fruity odor.

Toxicity Data With Reference

1.    

orl-rat LD50:1320 mg/kg

    FCTXAV    Food and Cosmetics Toxicology. 8 (1970),349.
2.    

ipr-rat LD50:350 mg/kg

    FCTXAV    Food and Cosmetics Toxicology. 8 (1970),349.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn, IrritantXi
Risk Statements: 22 
R22:Harmful if swallowed.
Safety Statements: 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: EL8925000
Hazard Note: Irritant
Poison by intraperitoneal route. Moderately toxic by ingestion. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

 Raspberry ketone (CAS NO.5471-51-2) is also named as 1-(4-Hydroxyphenyl)-3-butanone ; 1-(p-Hydroxyphenyl)-3-butanone ; 2-Butanone, 4-(4-hydroxyphenyl)- ; 2-Butanone, 4-(p-hydroxyphenyl)- ; 4-(3-Oxobutyl)phenol ; 4-(4-Hydroxyphenyl)-2-butanone ; 4-(p-Hydroxyphenyl)-2-butanone ; 4-(p-Hydroxyphenyl)-2-butanone (natural) ; 4-08-00-00506 (Beilstein Handbook Reference) ; AI3-31812 ; BRN 0776080 ; FEMA No. 2588 ; Frambinone ; Hydroxyphenylbutanone, p- ; NSC 26515 ; Oxyphenalon ; Rasketone ; Rheosmin ; UNII-7QY1MH15BG ; p-Hydroxybenzyl acetone . It is insoluble in water, soluble in ethanol, ether and volatile oil.