Raspberry ketone supplier | CasNO.5471-51-2

Name
Raspberry ketone
EINECS 226-806-4
CAS No. 5471-51-2
Article Data75
CAS DataBase
Density 1.088 g/cm³
Solubility Insoluble in water; Soluble in ethanol and diethyl ether
Melting Point 81-85 °C(lit.)
Formula C₁₀H₁₂O₂
Boiling Point 292.2 °C at 760 mmHg
Molecular Weight 164.204
Flash Point 122.9 °C
Transport Information
Appearance white to slightly yellow powder or needles
Safety 26-36/37/39
Risk Codes 22
Molecular Structure
Hazard Symbols Xn, Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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 methanol	A 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In sulfuric acid	93%

: 74432-58-9
4-(4-(benzyloxy)phenyl)butan-2-one

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride In water Industrial scale;	93%

: 52252-58-1
2-(4-Hydroxybenzyl)acetessigsaeure-ethylester

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

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

: 4-(3-oxobutyl)phenyl pivalate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 23℃; for 20h;	87%

: 22214-30-8
(E)-4-(4-hydroxyphenyl)-3-buten-2-one

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With methanol; formic acid; water; silica gel; palladium dichloride for 0.366667h; Irradiation; microwave;	84%
With nickel boride; hydrogen In methanol at 25℃; for 1h; chemoselective reaction;	75%
With baker's yeast; D-glucose; resin XAD 1180 In water at 28℃; for 24h;	50%
With hydrogen

: 59092-94-3
(+)-rhododendrol

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With phosphate buffer; Rhodococcus ruber DSM 44541 cells; acetone at 20℃; for 17h; pH=7.5;	83%
With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 In aq. buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	73%

: 4-((tert-butyldiphenylsilyl)oxy)benzyl 3-oxobutanoate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.75h; Solvent; Temperature; Reagent/catalyst;	82%

: 123-08-0
4-hydroxy-benzaldehyde

: 67-64-1
acetone

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Stage #1: 4-hydroxy-benzaldehyde; acetone With morpholin-4-ium 2,2,2-trifluoroacetate at 75℃; for 12h; Aldol condensation; Sealed vial; Stage #2: With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;	80%

: 4-((triisopropylsilyl)oxy)benzyl 3-oxobutanoate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 3h;	70%

: 4-((tert-butyldimethylsilyl)oxy)benzyl 3-oxobutanoate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.75h;	66%

: 590-90-9
1-Hydroxy-3-butanone

: 108-95-2
phenol

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With D218 resin In toluene at 80 - 120℃; for 7h; Temperature; Large scale;	65%
With aluminium trichloride

: 69617-84-1
rac-rhododendrol

A: 59092-94-3, 69617-84-1, 501-96-2
(R)-rhododendrol

B: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With phosphate buffer; Rhodococcus ruber DSM 44541 cells; acetone at 30℃; for 44h; pH=7.5;	A n/a B 44.5%
With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant; NADP In acetone at 50℃; for 24h; pH=8; Enzymatic reaction; enantioselective reaction;	A n/a B n/a

: 590-90-9
1-Hydroxy-3-butanone

: 108-95-2
phenol

A: 22409-85-4
4-phenoxybutan-2-one

B: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Zr(4+)-montmorillonite at 100℃; for 48h;	A 0.4% B 28%
Zr(4+)-montmorillonite at 100℃; for 48h; Product distribution; further cation-exchanged montmorillonites; also with 3-buten-2-one instead of 4-hydroxybutan-2-one;	A 0.4% B 28%
HCl treated montmorillonite at 130℃; under 1500.15 Torr; for 24h; Product distribution / selectivity;

...Expand

: 22409-85-4
4-phenoxybutan-2-one

A: 16982-89-1
4-methylchroman

B: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With aluminium(III) ion In various solvent(s) at 100℃; for 48h;	A 8% B 10%
With aluminium(III) ion In various solvent(s) at 100℃; for 48h; Product distribution; various substrates and catalysts;	A 8% B 10%

: 78-94-4
methyl vinyl ketone

: 108-95-2
phenol

A: 22409-85-4
4-phenoxybutan-2-one

B: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 50℃; for 11h; Product distribution;
Zr(4+)-montmorillonite at 100℃; for 48h;	A 13 % Chromat. B 16 % Chromat.

...Expand

1-<4-hydroxy-phenyl>-buten-(1)-one-(3): 1-<4-hydroxy-phenyl>-buten-(1)-one-(3)

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With sodium amalgam; water

1-<4-methoxy-phenyl>-butanone-(3): 1-<4-methoxy-phenyl>-butanone-(3)

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With aluminium trichloride; benzene

4-oxy-benzylidenacetone: 4-oxy-benzylidenacetone

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
With methanol; platinum Hydrogenation;
With diethyl ether; platinum Hydrogenation;
With methanol; palladium on activated charcoal Hydrogenation;

: 123-08-0
4-hydroxy-benzaldehyde

n-nonyl halide: n-nonyl halide

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / Heating 2: H2 / Pd/C / ethyl acetate View Scheme

: 63549-55-3
4-bromophenyl 2,2-dimethylpropanoate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / NaHCO3; NaHCO2; tetrabutylammonium bromide / Pd-benzothiazole carbene complex / 8 h / 130 °C 2: 87 percent / NaOH / methanol; H2O / 20 h / 23 °C View Scheme

: 108-95-2
phenol

perchlorate: perchlorate

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent / Zr4+-mont / pyridine / 12 h / 100 °C 2: 10 percent / Al3+-mont / various solvent(s) / 48 h / 100 °C / various substrates and catalysts View Scheme

: 598-32-3
2-hydroxy-3-butene

: 540-38-5
4-Iodophenol

A: 194279-78-2
C10H12O2

B: 1068658-05-8
C10H12O2

C: 7074-13-7
3-(4'-hydroxyphenyl)butan-2-one

D: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

Conditions

Conditions	Yield
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In water at 20℃; for 0.25h; Heck reaction; Stage #2: p-Iodophenol; Kaiser oxime-derived complex on resin base In water at 120℃; for 5h; Heck reaction; Further stages.;	A n/a B n/a C n/a D 81 % Spectr.

...Expand

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

: (1,3-(2)H5)-4-(4'-hydroxyphenyl)butan-2-one

Conditions

Conditions	Yield
With potassium hydroxide; water-d2 for 48h;	100%
With potassium hydroxide; water-d2 In 1,4-dioxane at 50℃; for 24h;

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

: 69617-84-1
rac-rhododendrol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2h; Solvent; Enzymatic reaction;	100%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.5h; Inert atmosphere;	95%
With sodium tetrahydroborate In methanol; water at 20℃; for 10h; Cooling with ice;	94%

: 75-77-4
chloro-trimethyl-silane

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

: 522617-84-1
4-(4-trimethylsilyloxyphenyl)butan-2-one

Conditions

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In tetrahydrofuran at 20℃; for 5h;	91%
With triethylamine In tetrahydrofuran at 20℃;

: 13154-24-0
triisopropylsilyl chloride

: 5471-51-2
4-(4-hydroxyphenyl)-2-oxobutane

: 1445875-25-1
4-(4-((triisopropylsilyl)oxy)phenyl)butan-2-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube;	100%
With 1H-imidazole at 20℃;	75%
With 1H-imidazole In dichloromethane at 23℃; Inert atmosphere;

Raspberry ketone Chemical Properties

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):

Raspberry ketone 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.

Raspberry ketone 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.

Raspberry ketone Consensus Reports

Reported in EPA TSCA Inventory.

Raspberry ketone Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
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.

Raspberry ketone Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

Raspberry ketone 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.

Product Name

Raspberry ketone

Synthetic route

Raspberry ketone Chemical Properties

Raspberry ketone Uses

Raspberry ketone Toxicity Data With Reference

Raspberry ketone Consensus Reports

Raspberry ketone Safety Profile

Raspberry ketone Standards and Recommendations

Raspberry ketone Specification

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