Vanillin

Base Information

• Chemical Name: Vanillin
• CAS No.: 121-33-5
• Deprecated CAS: 52447-63-9,8014-42-4,8014-42-4
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 2912.41 Oral rat LD50: 1580 mg/kg
• European Community (EC) Number: 204-465-2,693-906-6
• ICSC Number: 1740
• NSC Number: 403658,48383,15351
• UNII: CHI530446X
• DSSTox Substance ID: DTXSID0021969
• Nikkaji Number: J2.923H
• Wikipedia: Vanillin
• Wikidata: Q33495
• NCI Thesaurus Code: C76737
• RXCUI: 1368176
• Pharos Ligand ID: BLQH7W451Q4W
• Metabolomics Workbench ID: 41989
• ChEMBL ID: CHEMBL13883
• Mol file: 121-33-5.mol

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;

Chemical Property of Vanillin

Chemical Property:

• Appearance/Colour: White or very slightly yellow needles
• Vapor Pressure: >0.01 mm Hg ( 25 °C)
• Melting Point: 81-84 °C
• Refractive Index: Health: 1; Flammability: 1; Reactivity: 0
• Boiling Point: 282.6 °C at 760 mmHg
• PKA: pKa 7.396±0.004(H2O I = 0.00 t = 25.0±1.0) (Reliable)
• Flash Point: 117.6 °C
• PSA: 46.53000
• Density: 1.231 g/cm³
• LogP: 1.21330
• Storage Temp.: Refrigerator
• Sensitive.: Air & Light Sensitive
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: 10 g/L (25 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

97%Min ^*data from raw suppliers

Vanillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-36
• Safety Statements: 24/25-22-37/39-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=C(C=CC(=C1)C=O)O
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Description: Vanillin (4-hydroxy-3-methoxybenzaldehyde) is a known natural aromatic flavoring agent and the major component of vanilla extracted from cured vanilla pods.
• Nature and Applications: Vanillin is a natural aromatic flavoring agent and the major component of vanilla.; It finds applications in foods, beverages, pharmaceuticals, perfumes, and cosmetics.; It is considered safe by regulatory bodies like the FDA and FEMA.
• Chemical Properties: Vanillin is a specialized metabolite with functional groups like aldehyde, hydroxyl, and ether attached to an aromatic ring.; It can be isolated from vanilla extract or chemically synthesized from guaiacol.; It is a white or slightly yellow dry powder, soluble in various solvents.
• Bioactive Properties: Vanillin exhibits diverse bioactive properties including anticancer, neuroprotective, antibiotic potentiation, and anti-quorum sensing.; It is attributed to the constituent and stable degradation products of curcumin.
• Production Routes: Vanillin can be produced via chemical synthesis, vegetable biosynthesis, and biotechnological processes (bio-vanilla).; Bio-vanillin has advantages like being considered natural and utilizing industrial wastes.
• Industrial Usage: Industrially produced vanillin is used as a flavoring agent in various products including food, beverages, cigarettes, perfumes, and pharmaceuticals.; It is also used in the polymer industry, detergents, balms, and perfumes, depending on its type or source.
• Source: In cured vanilla beans, vanillin occurs in concentration of 1.0鈥?2.0% w/w.; It contributes to the vanilla flavor and is present alongside other compounds like vanillic acid, proteins, sugars, fibers, waxes, resins, pigments, tannins, minerals, vitamins, and essential oils.

Technology Process of Vanillin

There total 505 articles about Vanillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1,1-diacetoxy-1-(4-acetoxy-3-methoxyphenyl)methane (6301-73-1) → vanillin acetate (881-68-5) + vanillin (121-33-5,8014-42-4)

Guidance literature:

With aminosulfonic acid; In benzene; for 0.666667h; Heating;

Reference yield: 59.0%

4-hydroxymethyl-2-methoxyphenol (498-00-0) → 2-methoxy-1,4-benzoquinone (2880-58-2) + vanillin (121-33-5,8014-42-4)

Guidance literature:

With C₃₈H₅₈CoN₄O₂; oxygen; In methanol; at 20 ℃; for 16h; under 2585.81 Torr; Reagent/catalyst;

DOI:10.1039/c4gc00709c

Reference yield: 46.0%

2-methoxy-4-((E)-phenylethenyl)phenol (3391-75-1,18486-72-1) → benzaldehyde (100-52-7) + vanillin (121-33-5,8014-42-4)

Guidance literature:

With oxygen; CoSMDPT; In 1,2-dichloro-ethane; at 25 ℃; for 5h;

DOI:10.1016/S0040-4039(00)82415-6

upstream raw materials:

methanol

3-bromo-4-hydroxybenzylaldehyde

2,2,2-trichloro-1-(4-hydroxy-3-methoxy-phenyl)-ethanol

sodium methylate

Downstream raw materials:

3-methoxy-stilben-4-ol

4-hydroxy-3-methoxy-5-[(piperidin-1-yl)-methyl]benzaldehyde

2-methoxy-4-(piperidin-1-ylmethyl)phenol

2-morpholino-5-vanillylidene-thiazol-4-one

Refernces

• 1、 Vijayakumari,Reddy, Balakrishna,Nagarapu, Lingaiah. "Oxidative deoximation with H2O2 and MCM-41". . p. 407 - 410. Retrieved 2006.
• 2、 Sugata. "A chemical model of catechol-O-methyltransferase. Methylation of 3,4- dihydroxybenzaldehyde in methanol solution". . p. 1007 - 1011. Retrieved 1993.
• 3、 Filiciotto, Layla,Márquez-Medina, María Dolores,Pineda, Antonio,Balu, Alina M.,Romero, Antonio A.,Angelici, Carlo,de Jong, Ed,van der Waal, Jan C.,Luque, Rafael. "Continuous flow study of isoeugenol to vanillin: A bio-based iron oxide catalyst". . p. 281 - 290. Retrieved 2021.
• 4、 Hagiwara, Hisahiro,Sugawara, Yoshitaka,Isobe, Kohei,Hoshi, Takashi,Suzuki, Toshio. "Immobilization of Pd(OAc)2 in ionic liquid on silica: Application to sustainable Mizoroki-Heck reaction". . p. 2325 - 2328. Retrieved 2004.
• 5、 Haikarainen, Anssi,Sipil?, Jussi,Pietik?inen, Pekka,Pajunen, Aarne,Mutikainen, Ilpo. "Salen complexes with bulky substituents as useful tools for biomimetic phenol oxidation research". . p. 1633 - 1638. Retrieved 2001.
• 6、 Mao, Haifang,Wang, Hongzhao,Meng, Tao,Wang, Chaoyang,Hu, Xiaojun,Xiao, Zuobing,Liu, Jibo. "An efficient environmentally friendly CuFe2O4/SiO2catalyst for vanillyl mandelic acid oxidation in water under atmospheric pressure and a mechanism study". . p. 982 - 992. Retrieved 2021.
• 7、 Cadart, Timothée,Koukal, Petr,Kotora, Martin. "Enantioselective allylation of tert-butyldimethylsilyl-protected vanillin and synthesis of a lignan derivative isolated from machilus wangchiana". . p. 7556 - 7560. Retrieved 2014.
• 8、 Lee, Kyung-Seon,Rosazza, John P.N.. "Biocatalytic oxidation of 4-vinylphenol by Nocardia". . p. 582 - 588. Retrieved 2002.
• 9、 Yi, Fengping,Jiang, Xiaoyan,Niu, Jihua,Zhang, Lirong,Wang, Zhen. "New synthesis of vanillin by degradation of lignin in presence of functional basic ionic liquid". . p. 885 - 888. Retrieved 2015.
• 10、 Wang, Eng-Chi,Wu, Chien-Huang,Chien, Shih-Chang,Chiang, Wen-Chang,Kuo, Yueh-Hsiung. "An efficient and chemoselective deprotection of aryl- and styrenyldithioketals (acetals)". . p. 7706 - 7708. Retrieved 2007.