3-(4-Hydroxy-3-methoxyphenyl)-1-propanol supplier

Name
DIHYDROCONIFERYL ALCOHOL
EINECS
CAS No. 2305-13-7
Article Data50
CAS DataBase
Density 1.148 g/cm³
Solubility
Melting Point 63-65 °C
Formula C₁₀H₁₄O₃
Boiling Point 339.8 °C at 760 mmHg
Molecular Weight 182.219
Flash Point 159.3 °C
Transport Information
Appearance
Safety
Risk Codes R40; R22; R10; R36/38; R23/25; R11; R36/37/38
Molecular Structure
Hazard Symbols Xn,T,F,Xi
Synonyms Guaiacylpropanol;
PSA 49.69000
LogP 1.32570

Synthetic route

: 458-36-6
trans-coniferyl aldehyde

A: 2305-13-7
3-Guaiacylpropanol

B: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethyl acetate for 1h; Ambient temperature;	A 1% B 99%

: 7382-59-4
guaiacylglycerol-β-guaiacyl ether

A: 2785-87-7
2-methoxy-4-n-propylphenol

B: 2305-13-7
3-Guaiacylpropanol

C: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; zinc(II) acetate dihydrate In methanol at 225℃; under 26618.1 Torr; Catalytic behavior;	A 69% B 20% C 98%
With hydrogen In methanol at 260℃; under 22502.3 Torr; for 12h; Catalytic behavior; Temperature; Time;	A 43 %Chromat. B 11 %Chromat. C 71 %Chromat.
With hydrogen In methanol at 220℃; under 22502.3 Torr; for 8h; Catalytic behavior; Temperature;	A 11 %Chromat. B 44 %Chromat. C 76 %Chromat.

...Expand

: 7382-59-4
guaiacylglycerol-β-guaiacyl ether

A: 2305-13-7
3-Guaiacylpropanol

B: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With formic acid In water at 120℃; for 3h; Green chemistry;	A 93% B 95%
With palladium 10% on activated carbon; hydrogen In methanol at 225℃; under 26618.1 Torr; Catalytic behavior;	A 74% B 74%
With 10% nickel/activated carbon; hydrogen In 1,4-dioxane at 150℃; under 15001.5 Torr; for 2h; Autoclave;	A 7.7% B 6.4%

: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With ferrous ammonium sulphate hexahydrate; isopropyl β-D-thiogalactopyranoside In aq. phosphate buffer at 37℃; for 48h;	91%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 4h;	90%
With hydrogen; palladium on activated charcoal In ethyl acetate for 3h;	55 mg

: 56024-44-3
methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In water for 8h; Ambient temperature;	90%
With lithium aluminium tetrahydride In diethyl ether
With lithium borohydride In diethyl ether; toluene for 0.25h; Heating;
With lithium aluminium tetrahydride Reduction;

: 97-53-0
4-allylguaiacol

A: 2305-13-7
3-Guaiacylpropanol

B: 20736-21-4
1-(4-hydroxy-3-methoxyphenyl)-2-propanol

Conditions

Conditions	Yield
Stage #1: 4-allylguaiacol With dimethylsulfide borane complex In tetrahydrofuran Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran	A 84% B n/a
Stage #1: 4-allylguaiacol With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	A 80% B n/a
With sodium hydroxide; tetrabutylammonium boranate; dihydrogen peroxide; methyl iodide 1.) CH2Cl2, reflux, 30 min, 2.) 1.5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

: 1135-24-6
3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With whole cell cultures of dichomitus albidofuscus at 24℃; for 72h; Darkness; Microbiological reaction;	77%
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran / 1 h / -30 °C 2: H2 / 10percent Pd-charcoal / methanol / 2 h / 1810.02 Torr View Scheme
With D-Glucose; Escherichia coli endogenous alcohol dehydrogenase; Segniliparus rugosus carboxylic acid reductase; dimethyl sulfoxide; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Enzymatic reaction;

: 7382-59-4
guaiacylglycerol-β-guaiacyl ether

A: 2305-13-7
3-Guaiacylpropanol

B: 95316-34-0
3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan

C: 90-05-1
2-methoxy-phenol

Conditions

Conditions	Yield
With 10% nickel/activated carbon; hydrogen In methanol at 120℃; under 15001.5 Torr; for 2h; Time; Autoclave;	A 7.4% B 72.8% C 9.2%

...Expand

: 20649-42-7, 458-36-6
coniferaldehyde

A: 2305-13-7
3-Guaiacylpropanol

B: 80638-48-8
3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen for 2h;	A 70.4% B 11.9%

: 94824-16-5
1,3-dihydroxy-1-(4-O-benzyl-3-methoxyphenyl)propane

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With hydrogenchloride In water	45%

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

A: 458-36-6
trans-coniferyl aldehyde

B: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With D-glucose In aq. phosphate buffer at 30℃; for 16h; pH=8; Enzymatic reaction;	A n/a B 22%

: 64-17-5
ethanol

: 61292-90-8
ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium anschliessendes Kochen mit Wasser;

: 458-35-5
coniferol

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With ethanol; nickel Hydrogenation;
With tetrahydrofuran; palladium Hydrogenation;
With hydroxide; hydrogen; nickel In ethanol
With hydrogen; palladium on activated charcoal In methanol under 1810.02 Torr; for 2h;

: 1135-23-5
3-(4-hydroxy-3-methoxyphenyl)propionic acid

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride
Multi-step reaction with 2 steps 1: 98 percent H2SO4 2: LiAlH4 / diethyl ether View Scheme

: 61292-90-8
ethyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With ethanol; sodium

: 2-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzoic acid

: 2305-13-7
3-Guaiacylpropanol

: 7452-86-0
bis-[3-(4-hydroxy-3-methoxy-phenyl)-3-oxo-propyl]-ether

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium hydroxide; nickel at 165℃; under 154457 Torr; Hydrogenation;

: 5155-65-7
3.6-Bis-hydroxymethyl-2.5-bis-<4-hydroxy-3-methoxy-phenyl>-1.4-dithian

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium hydroxide; nickel In ethylene glycol

: Veratrylglycerin-β-dihydroconiferylether

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium hydroxide at 170℃;

: 97133-59-0, 135820-77-8, 135820-78-9, 79171-88-3, 2316-18-9
1-(4-hydroxy-3-methoxyphenyl)-2-<4-(ω-hydroxypropyl-2-methoxy)-phenoxy>-propane-1,3-diol

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium sulfide; sodium hydroxide at 135℃;

: 97-53-0
4-allylguaiacol

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With sodium hydroxide; dimethylsulfide; borane; dihydrogen peroxide other reagents: borane/THF, 9-borabicyclo<3.3.1>nonane; Multistep reaction;

3-<4-acetoxy-3-methoxy-phenyl>-propionyl chloride: 3-<4-acetoxy-3-methoxy-phenyl>-propionyl chloride

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With Trimethyl borate; sodium

maple wood: maple wood

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With ethanol; hydrogen; nickel at 170℃; under 154457 Torr;

: 60-29-7
diethyl ether

: 107682-24-6
ω-hydroxypropioguaiacone diacetate

LiAlH4: LiAlH4

A: 2305-13-7
3-Guaiacylpropanol

B: 3063-86-3
3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-1-propanol

...Expand

: 7452-86-0
bis-[3-(4-hydroxy-3-methoxy-phenyl)-3-oxo-propyl]-ether

aq.-ethanolic NaOH: aq.-ethanolic NaOH

Raney nickel: Raney nickel

A: 2785-87-7
2-methoxy-4-n-propylphenol

B: 2305-13-7
3-Guaiacylpropanol

C bis-<3-(4-hydroxy-3-methoxy-phenyl)-propyl>-ether: bis-<3-(4-hydroxy-3-methoxy-phenyl)-propyl>-ether

Conditions

Conditions	Yield
at 165℃; under 154457 Torr; Hydrogenation;

...Expand

forest plant material: forest plant material

A: 124-38-9
carbon dioxide

B: 201230-82-2
carbon monoxide

C: 2305-13-7
3-Guaiacylpropanol

D: 458-35-5, 32811-40-8, 69056-21-9
coniferal alcohol

Conditions

Conditions	Yield
With air Oxidation; Formation of xenobiotics; Further byproducts given;

...Expand

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: H+ 2: H2 / 10 percent Pd/C 3: LiAlH4 View Scheme
Multi-step reaction with 3 steps 1: aq. HCl / 6 h / Heating 2: H2 / 10percent Pd/C / methanol / 0.5 h / 760 Torr / Ambient temperature 3: LiBH4 / diethyl ether; toluene / 0.25 h / Heating View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 12 h / Reflux; Inert atmosphere 2: diisobutylaluminium hydride / dichloromethane; hexane / 3 h / -78 °C / Inert atmosphere 3: ferrous ammonium sulphate hexahydrate; isopropyl β-D-thiogalactopyranoside / aq. phosphate buffer / 48 h / 37 °C View Scheme

: 2309-07-1
Methyl ferulate

: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 10 percent Pd/C 2: LiAlH4 View Scheme
Multi-step reaction with 2 steps 1: H2 / 10percent Pd/C / methanol / 0.5 h / 760 Torr / Ambient temperature 2: LiBH4 / diethyl ether; toluene / 0.25 h / Heating View Scheme

poplar lignin: poplar lignin

A: 2785-87-7
2-methoxy-4-n-propylphenol

B: 6766-82-1
4-n-propylsyringol

C: 2305-13-7
3-Guaiacylpropanol

Conditions

Conditions	Yield
With rhodium on carbon; hydrogen In water at 199.84℃; under 25858.1 Torr; for 1h; Autoclave;
With rhodium on carbon; hydrogen In water at 199.84℃; under 25858.1 Torr; for 4h; Autoclave;

...Expand

: 2305-13-7
3-Guaiacylpropanol

: 46118-02-9
3-(3',4'-dihydroxyphenyl)-1-propanol

Conditions

Conditions	Yield
With zeolite beta (Zeolyst, CP814C) In water at 250℃; under 37503.8 Torr; for 6h; Reagent/catalyst; Sealed tube; Inert atmosphere;	98%

: 5963-14-4
8-methylnonanoic acid

: 2305-13-7
3-Guaiacylpropanol

: 951221-75-3
8-methylnonanoic acid 3-(4-hydroxy-3-methoxyphenyl)propyl ester

Conditions

Conditions	Yield
novozyme 435 at 50℃; for 16h; Enzymatic reaction; Neat (no solvent);	95.4%

: 2305-13-7
3-Guaiacylpropanol

: 106-95-6
allyl bromide

: 130447-88-0
3-(4-(allyloxy)-3-methoxyphenyl)propan-1-ol

Conditions

Conditions	Yield
With potassium carbonate In acetone	83%
With potassium carbonate; potassium iodide In acetone Reflux;	46%
With ethanol; potassium carbonate

: 2305-13-7
3-Guaiacylpropanol

: 141-78-6
ethyl acetate

: 14574-06-2
3-(4-hydroxy-3-methoxyphenyl)-propyl acetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; silica gel at 20℃; for 9h;	80%

: 2305-13-7
3-Guaiacylpropanol

: 7-methoxy-1-oxaspiro[4.5]deca-6,9-dien-8-one

Conditions

Conditions	Yield
With 1,1,3-trimethyl-3-phenylindan-4',5-dicarboxylic acid In dichloromethane	74%

: 2305-13-7
3-Guaiacylpropanol

: 2-(benzyloxy)-1-bromo-5-ethyl-3-methoxybenzene

: 3-(4-(2-(benzyloxy)-5-ethyl-3-methoxyphenoxy)-3-methoxyphenyl)propan-1-ol

Conditions

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 100℃; for 20h; Glovebox; Sealed tube;	74%

: 2305-13-7
3-Guaiacylpropanol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 4-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-methoxy-phenol

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane for 24h; silylation; 0 deg C up to RT;	55%

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 2305-13-7
3-Guaiacylpropanol

: (E)-3-(4-hydroxy-3-methoxyphenyl)propyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Mitsunobu Displacement; chemoselective reaction;	50%

: 2305-13-7
3-Guaiacylpropanol

: 530-59-6
trans-3,5-dimethoxy-4-hydroxycinnamic acid

: (E)-3-(4-hydroxy-3-methoxyphenyl)propyl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Mitsunobu Displacement; chemoselective reaction;	50%

: 2305-13-7
3-Guaiacylpropanol

: 555-16-8
4-nitrobenzaldehdye

: 960357-41-9
8-hydroxy-7-methoxy-1-(4-nitrophenyl)-1,3,4,5-tetrahydrobenzo[c]oxepine

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; aluminium trichloride In 1,4-dioxane at 20℃; for 168h; oxa-Pictet-Spengler reaction;	47%

: 2305-13-7
3-Guaiacylpropanol

: 80638-48-8
3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde

Conditions

Conditions	Yield
With dimethyl sulfoxide; triethylamine In dichloromethane at 20℃; for 0.5h;	27.5%
With coniferyl alcohol dehydrogenase isosyme I from cell free extract of Stretomyces sp. NL15-2K; nicotinamide adenine dinucleotide pH=9.5; Kinetics; Concentration; pH-value; Reagent/catalyst; Glycine-NaOH buffer; Enzymatic reaction;

: 110-86-1
pyridine

: 2305-13-7
3-Guaiacylpropanol

: 122-04-3
4-nitro-benzoyl chloride

: 22805-51-2
2-methoxy-1-(4-nitro-benzoyloxy)-4-[3-(4-nitro-benzoyloxy)-propyl]-benzene

...Expand

: 2305-13-7
3-Guaiacylpropanol

: 6245-54-1
2-hydroxy-5-(3-hydroxy-propyl)-3-methoxy-benzaldehyde

Conditions

Conditions	Yield
With potassium hydroxide; ethanol; chloroform
Multi-step reaction with 4 steps 1: K2CO3; ethanol 2: 240 °C 3: KOH; water / 170 - 175 °C 4: ozone; ethyl acetate / und Erwaermen des Reaktionsprodukts mit Wasser View Scheme

3-(4-Hydroxy-3-methoxyphenyl)-1-propanol Specification

The Benzenepropanol,4-hydroxy-3-methoxy-, with the CAS registry number of 2305-13-7, is also known as Guaiacylpropanol. It belongs to the product category of Benzhydrols, Benzyl & Special Alcohols. This chemical's molecular formula is C₁₀H₁₄O₃ and molecular weight is 182.22. What's more, its IUPAC name is 4-(3-Hydroxypropyl)-2-methoxyphenol.

Physical properties about the Benzenepropanol,4-hydroxy-3-methoxy- are: (1)ACD/LogP: 0.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.85; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 2.59; (6)ACD/BCF (pH 7.4): 2.59; (7)ACD/KOC (pH 5.5): 68.87; (8)ACD/KOC (pH 7.4): 68.73; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 27.69 Å²; (13)Index of Refraction: 1.549; (14)Molar Refractivity: 50.53 cm³; (15)Molar Volume: 158.6 cm³; (16)Surface Tension: 45.4 dyne/cm; (17)Density: 1.148 g/cm³; (18)Flash Point: 159.3 °C; (19)Enthalpy of Vaporization: 61.56 kJ/mol; (20)Boiling Point: 339.8 °C at 760 mmHg; (21)Vapour Pressure: 3.49E-05 mmHg at 25 °C.

Preparation: this chemical is prepared by 3-(4-Hydroxy-3-methoxy-phenyl)-propionic acid methyl ester. The reaction needs reagent LiBH₄ and solvent Diethyl ether. The reaction time is 15 min.

Uses: it is used to produce other chemicals. For example, it is used to produce 4-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-methoxy-phenol. This reaction needs reagents Et₃N and N,N-Dimethylaminopyridine. Meanwhile, it needs solvent CH₂Cl₂. The reaction time is 24 h. The yield is about 55 %.

You can still convert the following datas into molecular structure:
(1) SMILES: Oc1ccc(cc1OC)CCCO
(2) InChI: InChI=1/C10H14O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h4-5,7,11-12H,2-3,6H2,1H3
(3) InChIKey: MWOMNLDJNQWJMK-UHFFFAOYAL

Product Name

DIHYDROCONIFERYL ALCOHOL

Synthetic route

3-(4-Hydroxy-3-methoxyphenyl)-1-propanol Specification

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