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| Vanillic acid Basic information |
| Product Name: | Vanillic acid |
| Synonyms: | PROTOCATECHUIC ACID 3-METHYL ETHER;TIMTEC-BB SBB008280;RARECHEM AL BO 0061;VANILLIC ACID;VENILLIC ACID;4-HYDROXY-3-METHOXYBENZOIC ACID;AKOS BBS-00003785;FEMA 3988 |
| CAS: | 121-34-6 |
| MF: | C8H8O4 |
| MW: | 168.15 |
| EINECS: | 204-466-8 |
| Product Categories: | Phenols;Armoracia rusticana (Horseradish);Hordeum vulgare (Barley);s wort);Allium cepa (Onion);Allium sativum (Garlic);Aspalathus linearis (Rooibos tea);C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Cichorium intybus (Chicory);Curcuma longa (Turmeric);Elettaria Cardamomum (Cardamom);FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;BUILDING BLOCKS;BenzoicAcidDerivative;Organic acids;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Ginkgo biloba;Nutrition Research;Organic Building Blocks;Panax ginseng;Phytochemicals by Plant (Food/Spice/Herb);Vaccinium myrtillus (Bilberry);Zingiber officinale (Ginger);Building block;bc0001 |
| Mol File: | 121-34-6.mol |
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| Vanillic acid Chemical Properties |
| Melting point | 208-210 °C(lit.) |
| Boiling point | 257.07°C (rough estimate) |
| density | 1.3037 (rough estimate) |
| refractive index | 1.5090 (estimate) |
| FEMA | 3988 | 4-HYDROXY-3-METHOXYBENZOIC ACID |
| storage temp. | Store below +30°C. |
| solubility | Acetonitrile (Slightly), Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly） |
| form | Liquid |
| pka | pKa 4.53(H2O t = 25 c = 0.016–0.001) (Uncertain) |
| color | Clear colorless to brown, may darken during storage |
| Odor | at 100.00 %. dairy milky custard creamy powdery vanilla bean |
| Odor Type | creamy |
| Water Solubility | Soluble in water, alcohol and ether. |
| Merck | 14,9931 |
| JECFA Number | 959 |
| BRN | 2208364 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChIKey | WKOLLVMJNQIZCI-UHFFFAOYSA-N |
| LogP | 1.30 |
| CAS DataBase Reference | 121-34-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Benzoic acid, 4-hydroxy-3-methoxy-(121-34-6) |
| EPA Substance Registry System | Vanillic acid (121-34-6) |
| Safety Information |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 37/39-26-36 |
| WGK Germany | 1 |
| RTECS | YW5300000 |
| Hazard Note | Irritant |
| TSCA | Yes |
| HS Code | 29189090 |
| Vanillic acid Usage And Synthesis |
| Description | Vanillic acid is a dihydroxybenzoic acid that can be used as a flavoring agent. As an oxidized form of vanillin, it is the intermediate product during the two-step bioconversion process from ferulic acid to vanillin. It exists in high amount in the root of Angelica sinenisis, which is a plant used in traditional Chinese medicine. It also exists in acal oil, argan oil as well as wine and vinegar. It can be used in the synthesis of the analeptic drug etamivan, modecainide, brovanexine, vanitiolide, and vanyldisulfamide. It can be manufactured through the oxidation of vanillin to the carboxylic acid. |
| References | https://en.wikipedia.org/wiki/Vanillic_acid https://pubchem.ncbi.nlm.nih.gov/compound/Vanillic_acid#section=Top |
| Chemical Properties | white odourless crystals or powder |
| Chemical Properties | 4-Hydroxy-3-methoxybenzoic acid has a vanilla-like odor and taste. |
| Occurrence | Reported found in guava, grape, brandy, rum, whiskey, sherry, red and white wines, Scotch and Canadian whiskey, pork (fried), cocoa, peanuts (raw), mushrooms, guava fruit, mangos (fresh), wort, vanilla and black chokeberries. |
| Uses | Vanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, an d antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent. |
| Uses | A flavoring agent. |
| Uses | Vanillic acid is used as a flavoring agent in food. It acts as an intermediate in the production of vanillin from ferulic acid. Further, it is used in wine and vinegar. |
| Preparation | Prepared by bioconversion of ferulic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BS13. Also prepared by whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus |
| Definition | ChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. |
| Aroma threshold values | Aroma at 5.0%: weak vanilla, creamy, milky. |
| Taste threshold values | Taste characteristics at 100 ppm: weak sweet resinous vanilla, creamy with a smooth sweetness and body, slightly chocolate-like with a spicy vanitrop nuance |
| Synthesis Reference(s) | Journal of the American Chemical Society, 68, p. 429, 1946 DOI: 10.1021/ja01207a025 Organic Syntheses, Coll. Vol. 4, p. 972, 1963 |
| General Description | Vanillic acid is one of the key aromatic volatile compounds of vanilla beans. |
| Biochem/physiol Actions | Taste at 100 ppm |
