4-Hydroxybenzoic acid CAS 99-96-7
Introduction：Basic information about 4-Hydroxybenzoic acid CAS 99-96-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
4-Hydroxybenzoic acid Basic information
| Product Name: | 4-Hydroxybenzoic acid |
| Synonyms: | 4-hydroxy-benzoicaci;acidop-idrossibenzoico;Benzoic acid, p-hydroxy-;benzoicacid,4-hydroxy;Benzoicacid,4-hydroxy-;Hydroxybenzoic acid, para;Kyselina 4-hydroxybenzoova;kyselina4-hydroxybenzoova |
| CAS: | 99-96-7 |
| MF: | C7H6O3 |
| MW: | 138.12 |
| EINECS: | 202-804-9 |
| Product Categories: | Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Allium cepa (Onion);Allium sativum (Garlic);Armoracia rusticana (Horseradish);Aspalathus linearis (Rooibos tea);Cichorium intybus (Chicory);Elettaria Cardamomum (Cardamom);Ginkgo biloba;Hordeum vulgare (Barley);Linum usitatissimum (Flax);Benzoic acid Series;Chemistry;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;C7;Carbonyl Compounds;Alphabetical Listings;Flavors and Fragrances;G-H;sy;Nutrition Research;Phytochemicals by Plant (Food/Spice/Herb);s wort);Vaccinium myrtillus (Bilberry);Pharmaceutical Raw Materials;Benzoic Acids (Building Blocks for Liquid Crystals);Bifunctional Compounds (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Phenols (Building Blocks for Liquid Crystals);Carboxylic Acids;Zingiber officinale (Ginger);alcohol| carboxylic acid;Inhibitors;p-Hydroxybenzoi;1;99-96-7 |
| Mol File: | 99-96-7.mol |
4-Hydroxybenzoic acid Chemical Properties
| Melting point | 213-217 °C (lit.) |
| Boiling point | 213.5°C (rough estimate) |
| bulk density | 600kg/m3 |
| density | 1,46 g/cm3 |
| vapor pressure | 0Pa at 20℃ |
| refractive index | 1.4600 (estimate) |
| FEMA | 3986 | 4-HYDROXYBENZOIC ACID |
| Fp | 199 °C |
| storage temp. | Store below +30°C. |
| solubility | methanol: soluble5%, clear to slightly hazy, colorless to faintly yellow |
| pka | 4.48(at 19℃) |
| form | Crystalline Powder |
| color | White to ivory |
| PH | 3.3 (1g/l, H2O, 20℃) |
| Odor | at 100.00 %. phenolic nutty |
| Odor Type | phenolic |
| biological source | synthetic |
| Water Solubility | 5 g/L (20 ºC) |
| Merck | 14,4812 |
| JECFA Number | 957 |
| BRN | 970950 |
| Cosmetics Ingredients Functions | PRESERVATIVE FRAGRANCE |
| Cosmetic Ingredient Review (CIR) | 4-Hydroxybenzoic acid (99-96-7) |
| InChI | 1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) |
| InChIKey | FJKROLUGYXJWQN-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccc(O)cc1 |
| LogP | 0.878 at 22℃ |
| CAS DataBase Reference | 99-96-7(CAS DataBase Reference) |
| NIST Chemistry Reference | Benzoic acid, 4-hydroxy-(99-96-7) |
| EPA Substance Registry System | p-Hydroxybenzoic acid (99-96-7) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36-36/37/38 |
| Safety Statements | 26-37/39-36 |
| WGK Germany | 1 |
| RTECS | DH1925000 |
| Autoignition Temperature | >250 °C |
| TSCA | TSCA listed |
| HS Code | 29182930 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 STOT SE 3 |
| Hazardous Substances Data | 99-96-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| Description | 4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid or PHBA, is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohol and acetone. It is isomeric with salicylic acid (2-hydroxybenzoic acid), a forerunner to aspirin, and 3-hydroxybenzoic acid. The esters of 4-hydroxybenzoic acid, also called parabens, are widely used as preservatives in cosmetics and some ophthalmic solutions. |
| Chemical Properties | 4-Hydroxybenzoic acid is an odorless white crystalline astringent powder. In pure form, it imparts a sweetish taste atfirst, which quickly becomes acrid and disagreeable |
| Occurrence | 4-Hydroxybenzoic acid is a phenolic acid that has been found in a variety of fruit peels and leaves. It can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in Macrotyloma uniflorum (horse gram), carob and in Phyllanthus acidus (Otaheite gooseberry). |
| Uses | 4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4'-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions. |
| Uses | In organic. syntheses; intermediate for dyes, fungicides. |
| Uses | p-Hydroxybenzoic acid is of significant commercial importance. The most familiar application is the use of several of its esters as preservatives, known as parabens. Also of interest is the use in liquid crystal polymer applications. |
| Definition | ChEBI: 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. |
| Preparation | Prepared from p-bromophenol or p-hydroxybenzaldehyde, or from saponification of methyl salicylate, a major componentof oil of wintergreen. In 1947, H. Gilman and C. E. Arntzen at Iowa State College (Ames) reported the synthesis of 4-HBA from 4-hydroxybenzaldehyde. Several other preparation methods were developed since then. Today it is produced commercially via the Kolbe–Schmitt reaction, which originated in the mid-1800s. Potassium phenoxide and CO2 are heated under pressure; the reaction mixture is then acidified to obtain the product 4-Hydroxybenzoic acid. (Oddly, if the sodium salt is used, the product is 2-hydroxybenzoic acid, or salicylic acid.) Org. Synth. 1934, 14, 48 DOI: 10.15227/orgsyn.014.0048 |
| Application | 4-Hydroxybenzoic acid can be used as a starting material to synthesize organic intermediates such as 4-acetoxybenzoic acid and 4-hydroxy-3,5-diiodobenzoic acid. 4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4′-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions. |
| Aroma threshold values | Detection at 5 ppm (water) |
| Synthesis Reference(s) | Journal of the American Chemical Society, 106, p. 174, 1984 DOI: 10.1021/ja00313a035 The Journal of Organic Chemistry, 29, p. 3459, 1964 DOI: 10.1021/jo01035a003 |
| General Description | Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. 4-Hydroxybenzoic acid belongs to the class of aromatic acids, which may be used as a preservative in cosmetics, pharmaceuticals and as a synthetic flavoring agent in food products. |
| Flammability and Explosibility | Non flammable |
| Purification Methods | Crystallise the hydroxyacid from water. [Beilstein 10 IV 345.] |
4-Hydroxybenzoic acid Preparation Products And Raw materials
| Raw materials | Potassium hydroxide-->Phenol-->Tosyl chloride-->Potassium hydroxide solution-->Potassium sulfate-->Saccharin-->Dipotassium rabdosiin Rabdosiin-->potassium phenolate-->Methyl 4-bromobenzoate-->4-Iodobenzoic acid-->4-(3-BUTENYLOXY)BENZOIC ACID-->4-BENZYLOXYBENZOIC ACID |
| Preparation Products | Bromoxynil-->4-Cyanophenol-->Ethylparaben-->4-Methoxybenzoic acid-->CYANOPHOS-->2-Bromobenzonitrile-->Methylparaben-->Propylparaben-->Isobutylparaben-->Isopropylparaben-->Butylparaben-->Heptyl 4-hydroxybenzoate-->4-N-BUTOXYBENZOIC ACID-->Sorbic acid |
