Vanillin

IUPAC Name: 4-Hydroxy-3-methoxybenzaldehyde
Synonyms of Vanillin (CAS NO.121-33-5): 2-Methoxy-4-formylphenol ; 3-Methoxy-4-hydroxybenzaldehyde ; 4-Formyl-2-methoxyphenol ; 4-Hydroxy-3-methoxybenzaldehyde ; 4-Hydroxy-5-methoxybenzaldehyde ; 4-Hydroxy-m-anisaldehyde ; Benzaldehyde, 4-hydroxy-3-methoxy- ; Methylprotocatechuic aldehyde ; Protocatechualdehyde 3-methyl ether ; m-Anisaldehyde, 4-hydroxy- ; p-Hydroxy-m-methoxybenzaldehyde
CAS NO: 121-33-5
Molecular Formula: C₈H₈O₃
Molecular Weight: 152.14
Molecular Structure:
EINECS: 204-465-2
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 3
Polar Surface Area: 46.53 Å²
Index of Refraction: 1.587
Molar Refractivity: 41.56 cm³
Molar Volume: 123.5 cm³
Surface Tension: 47.3 dyne/cm
Density: 1.231 g/cm³
Flash Point: 117.6 °C
Enthalpy of Vaporization: 54.25 kJ/mol
Boiling Point: 282.6 °C at 760 mmHg
Vapour Pressure: 0.00194 mmHg at 25°C
Melting Point: 81-84°C 
Water Solubility: 10 g/L (25°C )
Sensitive: Air & Light Sensitive
Stability: Stable. May discolour on exposure to light. Moisture-sensitive. Incompatible with strong oxidizing agents, perchloric acid.
Appearance: White or very slightly yellow needles.
Product Categories of Vanillin (CAS NO.121-33-5): FOOD ADDITIVES;PHARMACEUTICALS;Food and Feed Additive;FINE Chemical & INTERMEDIATES;Food & Feed ADDITIVES;Aromatic Aldehydes & Derivatives (substituted);Analytical Chemistry;TLC Stains;Food & Flavor Additives

  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.

 Vanillin (CAS NO.121-33-5) 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.

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.
 

Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 24/25-22-37/39-26
24/25: Avoid contact with skin and eyes 
22: Do not breathe dust 
37/39: Wear suitable gloves and eye/face protection 
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:  1
RTECS: YW5775000
HS Code: 29124100

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Dangerous fire hazard in the form of dust when exposed to heat or flame.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container. Store under an inert atmosphere.