Vanillin

  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.

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: