CAS No.121-33-5,Vanillin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	121-33-5
Name:	Vanillin
Article Data:	595

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:	Xn,Xi
Risk Codes:	22-36/37/38
Safety:	24/25-22-37/39-26
PSA:	46.53000
LogP:	1.21330

Synthetic route

: 498-00-0
4-hydroxymethyl-2-methoxyphenol

: 121-33-5
vanillin

Conditions

Conditions	Yield
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

Conditions	Yield
With dihydrogen peroxide; [(t-C4H9)4N]3PMo4O16 In tert-butyl alcohol	100%
With potassium hydroxide; nitrobenzene at 120 - 130℃;

: 881-68-5
vanillin acetate

: 121-33-5
vanillin

Conditions

Conditions	Yield
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

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

vanillin: vanillin

Conditions

Conditions	Yield
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

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

...Expand

: 2426-87-1
3-methoxy-4-(phenylmethoxy)benzaldehyde

: 121-33-5
vanillin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Raw Materials

458-36-6

71-43-2

75-85-4

Downstream Products

591-31-1

513-85-9

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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.