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121-33-5

Basic Information
CAS No.: 121-33-5
Name: Vanillin
Molecular Structure:
Molecular Structure of 121-33-5 (Vanillin)
Formula: C8H8O3
Molecular Weight: 152.15
Synonyms: 3-Methoxy-4-hydroxybenzaldehyde;p-Hydroxy-m-methoxybenzaldehyde;Benzaldehyde, 4-hydroxy-3-methoxy-;m-Anisaldehyde, 4-hydroxy-;4-Hydroxy,3-methoxy-benzaldehyde;4-Formyl-2-methoxyphenol;Vanillaldehyde;Benzaldehyde,4-hydroxy-3-methoxy-;p-vanillin;4-hydroxy-3-methoxy-benzaldehyde;4-Hydroxy-m-anisaldehyde;Protocatechualdehyde, methyl-;2-Methoxy-4-formylphenol;methylprotocatechuic aldehyde;4-Hydroxy-5-methoxybenzaldehyde;Vanillin FCC4;4-Hydroxy-3-methoxyBenzaldehyde;Vanillin natural;Methylproto-catechualdehyde;Vanillinum;3-Methoxy-4-hydroxybenzaldehyde( Vanillin);Vainillin;
EINECS: 204-465-2
Density: 1.231 g/cm3
Melting Point: 81-84 °C
Boiling Point: 282.6 °C at 760 mmHg
Flash Point: 117.6 °C
Solubility: methanol: 0.1 g/mL, clear
Appearance: White or very slightly yellow needles
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 24/25-22-37/39-26
Transport Information:
PSA: 46.53000
LogP: 1.21330
Synthetic route
498-00-0

4-hydroxymethyl-2-methoxyphenol

121-33-5

vanillin

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 40℃; for 8h; Catalytic behavior; Reagent/catalyst;100%
With palladium; oxygen; sodium hydrogencarbonate In water at 80℃; for 6h; Reagent/catalyst;100%
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation;99%
5932-68-3

(E)-2-methoxy-4-(1-propenyl)phenol

121-33-5

vanillin

Conditions
ConditionsYield
With dihydrogen peroxide; [(t-C4H9)4N]3PMo4O16 In tert-butyl alcohol100%
With potassium hydroxide; nitrobenzene at 120 - 130℃;
881-68-5

vanillin acetate

121-33-5

vanillin

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.5h; Hydrolysis; Heating;100%
With cucumber juice at 30 - 35℃; for 6h; Inert atmosphere; Green chemistry;94%
natural kaolinitic clay In methanol at 25℃; for 0.5h;90%

121-33-5

vanillin

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%

vanillin

vanillin

Conditions
ConditionsYield
With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 0.166667h; micellar medium;100%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 1h; Micellar solution;95%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.666667h;95%

O-[3-(3,4-methylenedioxyphenyl)-2-propenyl]vanillin

67-56-1

methanol

A

40581-87-1

5-(1-Methoxy-allyl)-benzo[1,3]dioxole

B

121-33-5

vanillin

C

84782-36-5

trans-1,2-methylenedioxy-4-(3'-methoxy-1'-propenyl)benzene

Conditions
ConditionsYield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) at 20℃; for 1.5h;A n/a
B 100%
C n/a
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

121-33-5

vanillin

Conditions
ConditionsYield
With iron(III) chloride on silica In neat (no solvent) at 30℃; for 1h;99%
With iron(III) chloride on silica In neat (no solvent) at 30℃; for 1h; other benzyloxy aromatics;99%
With methanol; amberlyst-15 In toluene at 110℃; for 2h;98%

2-methoxy-4-(prop-1-enyl)phenyl acetate

121-33-5

vanillin

Conditions
ConditionsYield
Stage #1: 2-methoxy-4-(prop-1-enyl)phenyl acetate With ozone In ethanol at -20 - 0℃;
Stage #2: With sodium metabisulfite In ethanol at 60 - 70℃;
Stage #3: With potassium carbonate at 85℃; for 4h; Temperature; Reagent/catalyst;
99%
90-05-1

2-methoxy-phenol

298-12-4

Glyoxilic acid

121-33-5

vanillin

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol; Glyoxilic acid With sodium hydroxide In water at 35 - 70℃; for 5h;
Stage #2: In water at 80℃; under 5250.53 Torr; pH=12; High pressure;
Stage #3: With sulfuric acid at 60℃; for 0.5h; pH=4;
98.9%
With sodium hydroxide und Erwaermen des Reaktionsprodukts mit Nitrohydroxybenzolsulfonsaeure und wss.NaOH oder mit CuSO4 und wss.NaOH;
2973-78-6

3-bromo-4-hydroxybenzylaldehyde

124-41-4

sodium methylate

121-33-5

vanillin

Conditions
ConditionsYield
With copper(II) carbonate; copper(II) hydroxide; carbon dioxide In methanol at 125℃; for 3h;98%
With Methyl formate; copper(l) chloride In methanol at 115℃; for 2h; Reagent/catalyst; Autoclave;98%
2874-33-1

vanillin oxime

121-33-5

vanillin

Conditions
ConditionsYield
With water; dihydrogen peroxide; iodine In acetonitrile at 20℃; for 6h;98%
With N-Bromosuccinimide; water at 20℃; for 0.0333333h; Hydrolysis;96%
With perchloric acid; dihydrogen peroxide; potassium bromide; ammonium molybdate tetrahydrate In water at 20℃; for 5h;90%
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

121-33-5

vanillin

Conditions
ConditionsYield
With tricopper(II) bis(benzene-1,3,5-tricarboxylate) trihydrate; dihydrogen peroxide In ethanol; water; acetonitrile at 100℃; for 1h;98%
With dihydrogen peroxide In ethanol; water; acetonitrile for 4h; Mechanism; Kinetics; Reflux;71%
titanium(IV) oxide In water at 65℃; under 3.75038 Torr; Irradiation;
5533-00-6

3-methoxy-4-methoxymethoxy-benzaldehyde

121-33-5

vanillin

Conditions
ConditionsYield
With silica-immobilized p-TsOH In toluene at 40℃; for 5h;97%
With Montmorillonite K 10 In benzene at 50℃; for 1h;96%
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.25h;95%
1696-60-2

vanillin azine

121-33-5

vanillin

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;97%

vanisal sodium

121-33-5

vanillin

Conditions
ConditionsYield
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation;97%
With ammonium acetate for 0.0025h; microwave irradiation;96%

C17H20O4

121-33-5

vanillin

Conditions
ConditionsYield
With silica-OSO3H; silica gel In toluene at 60 - 70℃; for 1h;97%
With tetrachlorosilane; silica gel In toluene at 60 - 70℃; for 1.16667h;92%
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; aluminium trichloride In acetonitrile Heating;

O-[3-(3,4-methylenedioxyphenyl)-2-propenyl]vanillin

67-56-1

methanol

A

121-33-5

vanillin

B

84782-36-5

trans-1,2-methylenedioxy-4-(3'-methoxy-1'-propenyl)benzene

C

4043-71-4

isosafrole

Conditions
ConditionsYield
With potassium hydroxide; palladium on activated charcoal at 20℃; for 10h;A 97%
B 7%
C 79%
69404-94-0

O-tert-butyldimethylsilylvanillin

121-33-5

vanillin

Conditions
ConditionsYield
With CH3O3S(1-)*C27H53N2O12(1+); cesium fluoride In tert-Amyl alcohol at 70℃; for 0.25h; chemoselective reaction;96%
With triethylamine N-oxide In methanol for 2h;95%
With 2,2,2-trifluoroethanol In N,N-dimethyl-formamide; toluene at 120℃; under 26252.6 Torr; for 0.0833333h; Flow reactor;90%
22280-95-1

4-allyloxy-3-methoxybenzaldehyde

121-33-5

vanillin

Conditions
ConditionsYield
With potassium hydroxide; palladium on activated charcoal In methanol at 20℃; for 9h;96%
With potassium hydroxide; palladium on activated charcoal In methanol at 20℃; for 8h;96%
With ammonium formate; palladium on activated charcoal In methanol at 25℃; for 6h;85%
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;65%
16742-60-2, 120445-66-1

vanillin semicarbazone

121-33-5

vanillin

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;95%
With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide In water; acetic acid at 20℃; for 5h;78%
85377-07-7

Vanillin acetal

121-33-5

vanillin

Conditions
ConditionsYield
With polyaniline-sulfate salt; water for 0.666667h; Heating;95%
129047-38-7

3-methoxy 4-((4-methoxybenzyl)oxy)benzaldehyde

121-33-5

vanillin

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane at 20℃; for 0.166667h; Solvent;95%
With oxalyl dichloride In 1,2-dichloro-ethane at 20℃; for 2.66667h;91%
With methanol; amberlyst-15 In toluene at 110℃; for 6h;86%
55-10-7

4-hydroxy-3-methoxy-mandelic acid

A

121-34-6

3-methoxy-4-hydroxybenzoic acid

B

121-33-5

vanillin

Conditions
ConditionsYield
With oxygen; 12.5% CuFe2O4/SiO2; sodium hydroxide In water at 90℃; under 750.075 Torr; for 3h; pH=11; Catalytic behavior; pH-value; Pressure; Reagent/catalyst; Temperature; Time; Green chemistry;A n/a
B 94.7%
With bismuth; oxygen; acetic acid In water; dimethyl sulfoxide at 125℃; under 760 Torr; for 0.333333h; Product distribution; Further Variations:; reaction time;
With sodium hydroxide; oxygen; CoCl2 In water; dimethyl sulfoxide at 125℃; under 760.051 Torr; for 2h; Title compound not separated from byproducts.;
With oxygen; BiIII-phthalate In dimethyl sulfoxide at 125℃; under 760.051 Torr; for 24h;
77-78-1

dimethyl sulfate

139-85-5

3,4-dihydroxybenzaldehyde

A

621-59-0

isovanillin

B

121-33-5

vanillin

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 1.58333h;A 93.5%
B 5.8%
With MES buffer In ethanol; water at 37℃; Kinetics; Thermodynamic data; O-methylation in the absence or in the presence of metal ion, ΔH(excit.), ΔS(excit.);
With HCl methanol buffer; BIS-TRIS at 37℃; Rate constant; Thermodynamic data; Kinetics; other divalent metal ions catalysts, var. temperat.; Ea, ΔH(excit.), ΔS(excit.);
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 5h;A 8 %Chromat.
B 77.5 %Chromat.

3-Methoxy-4-phenylsulfanylmethoxy-benzaldehyde

121-33-5

vanillin

Conditions
ConditionsYield
With mercury dichloride In acetonitrile Heating;93%
55-10-7

4-hydroxy-3-methoxy-mandelic acid

121-33-5

vanillin

Conditions
ConditionsYield
With ammonium metavanadate; oxygen In water at 80℃; under 5250.53 Torr; for 3h; Reagent/catalyst; Solvent;93%
With sodium periodate; potassium phosphate buffer; potassium carbonate In water at 25℃; Mechanism; other α-hydroxy acids; initial velocities; relative affinities of the different monoclonal antibodies;
With oxygen; acetic acid; bismuth In water; dimethyl sulfoxide at 125℃; under 760.051 Torr; for 0.333333h;
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  • Casno:

    121-33-5

    121-33-5 Vanillin

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    Specifications CAS No.: 121-33-5 Other Names: 4-Hydroxy-3-methoxybenzaldehyde MF: C8H8O3 EINECS No.: 204-465-2

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    121-33-5

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    121-33-5

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  • Vanillin

  • Casno:

    121-33-5

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History

  Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by Hernán Cortés, the Aztecs used it as a flavoring for chocolate. Europeans became aware of both chocolate and vanilla around the year 1520.
  Vanillin was first isolated as a relatively pure substance in 1858 by Nicolas-Theodore Gobley. In 1874, the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin, a glycoside of isoeugenol found in pine bark. In 1876, Karl Reimer synthesized vanillin from guaiacol.By the late 19th century, semisynthetic vanillin derived from the eugenol found in clove oil was commercially available.
Synthetic vanillin became significantly more available in the 1930s.By 1981, a single pulp and paper mill in Ontario supplied 60% of the world market for synthetic vanillin.Most synthetic vanillin is today synthesized in a two-step process from the petrochemical precursors guaiacol and glyoxylic acid.
Beginning in 2000, Rhodia began marketing biosynthetic vanillin prepared by the action of microorganisms on ferulic acid extracted from rice bran.

Specification

The Vanillin, with the CAS registry number 121-33-5,is also known as 4-Hydroxy-3-methoxybenzaldehyde. It belongs to the product categories of Phytochemicals by Plant (Food/Spice/Herb);Vaccinium myrtillus (Bilberry). This chemical's molecular formula is C8H8O3 and molecular weight is 152.14.Its EINECS number is 204-465-2. What's more,Its systematic name is Vanillin. It is a white crystals with vanilla odour.And it is stable,Incompatible with strong oxidizing agents, perchloric acid and moisture-sensitive. Also it may discolour on exposure to light.

Physical properties about Vanillin are:
(1)ACD/LogP:  1.208; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  1.21; (4)ACD/LogD (pH 7.4):  1.06; (5)ACD/BCF (pH 5.5):  4.85; (6)ACD/BCF (pH 7.4):  3.45; (7)ACD/KOC (pH 5.5):  107.64; (8)ACD/KOC (pH 7.4):  76.43; (9)#H bond acceptors:  3; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  3; (12)Index of Refraction:  1.587; (13)Molar Refractivity:  41.566 cm3; (14)Molar Volume:  123.532 cm3; (15)Surface Tension:  47.3310012817383 dyne/cm; (16)Density:  1.232 g/cm3; (17)Flash Point:  117.603 °C; (18)Enthalpy of Vaporization:  54.246 kJ/mol; (19)Boiling Point:  282.646 °C at 760 mmHg; (20)Vapour Pressure:  0.0020000000949949 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Oc1ccc(cc1OC)C=O;
(2)Std. InChI:InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3;
(3)Std. InChIKey:MWOOGOJBHIARFG-UHFFFAOYSA-N.

Safety Information of Vanillin:
The Vanillin is harmful if swallowed and irritating to eyes, respiratory system and skin.When you use it , you should avoid contact with skin and eyes,wear suitable gloves and eye/face protection ,and do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Production of Vanillin:
Natural production: Natural vanillin is extracted from the seed pods of Vanilla planifola, a vining orchid native to Mexico. First, the seed pods are blanched in hot water, to arrest the processes of the living plant tissues. Then, for 1–2 weeks, the pods are alternately sunned and sweated: during the day, they are laid out in the sun, and each night, wrapped in cloth and packed in airtight boxes to sweat. During this process, the pods become a dark brown, and enzymes in the pod release vanillin as the free molecule. At last, the pods are dried and further aged for several months, during which time their flavors further develop. Vanillin accounts for about 2% of the dry weight of cured vanilla beans, and is the chief among about 200 other flavor compounds found in vanilla.
Chemical synthesis: Today most vanillin is produced from the petrochemical raw material guaiacol.
  

Uses of Vanillin:
Vanillin is used as well as ethylvanillin in the food industry. Vanillin can use as a flavoring and is also used in the fragrance industry,in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products.Besides, Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals. Vanillin can be still used as a general purpose stain for developing thin layer chromatography (TLC) plates to aid in visualizing components of a reaction mixture.

The toxicity data of Vanillin are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 1320mg/kg (1320mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

VASCULAR: ACUTE ARTERIAL OCCLUSION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 2549, 1953.
guinea pig LD50 oral 1400mg/kg (1400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LC inhalation > 41700ug/kg/2 (41.7mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(6), Pg. 78, 1980.
mouse LD50 intraperitoneal 475mg/kg (475mg/kg)   FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 78, 1967.
mouse LD50 oral 3925mg/kg (3925mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: COMA
National Technical Information Service. Vol. OTS0536271,
rabbit LD50 skin > 5010mg/kg (5010mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: PERITONITIS

BEHAVIORAL: FOOD INTAKE (ANIMAL)
National Technical Information Service. Vol. OTS0533712,
rabbit LDLo oral 3gm/kg (3000mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 425, 1940.
rat LC inhalation > 41700ug/kg/4 (41.7mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(6), Pg. 78, 1980.
rat LD skin > 2gm/kg (2000mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" National Technical Information Service. Vol. OTS0536272,
rat LD50 intraperitoneal 1160mg/kg (1160mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 243, Pg. 609, 1956.
rat LD50 oral 1580mg/kg (1580mg/kg) BEHAVIORAL: COMA Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rat LD50 subcutaneous 1500mg/kg (1500mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896.