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Hydron benzoate

HCID 20144841
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Basic information

CAS
65-85-0
Standard SMILES
O=C([O-])c1ccccc1.[H+]
InChIKey
WPYMKLBDIGXBTP-UHFFFAOYSA-N
Molecular formula
C7H6O2
Average molar mass
122.12 g/mol
Monoisotopic mass
122.03677943

Overview

A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Names & identifiers

Preferred name
Hydron benzoate
IUPAC
hydron benzoate
English name
Benzoic acid
Molecular formula
C7H6O2
Molecular weight
122.12

Names & synonyms

SCHEMBL10633068Benzyl acidAcide benzoiqueBenzoesaeureBenzoic acid, for analysis ACSNipacideBenzoic aBenzoic acidcidFEMA 2131a 1 (acid)Benzoic acid naturalBenzoesure

Database identifiers

CAS
65-85-0
PubChem CID
20144841

Properties

Computed structural properties

Topological polar surface area
40.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
9
Formal charge
0
Complexity
98

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP1.87
Solubility3.4 mg/mL at 25 °C
Melting Point122.4 °C
Physical DescriptionSolid
Dissociation Constants4.19 (at 25 °C)

Physicochemical properties

Melting point
121 · 121-125 °C(lit.)
Boiling point
249 °C · 249 °C(lit.)
Density
1.08 · 1.08
bulk density
500 kg/m3 · 500kg/m3
vapor density
4.21 · 4.21 (vs air)
vapor pressure
10 mm · 10 mm Hg ( 132 °C)
refractive index
1.504 · 1.504
FEMA
2131 · 2131 | BENZOIC ACID

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
21
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
DG0875000
ridadr
UN 3077 9/PG 3
hs_code
2916 31 00
Toxicity
LD50 orally in Rabbit: 1700 mg/kg LD50 dermal Rabbit > 5000 mg/kg
risk_code
22-36-42/43-36/37/38-40-63-43-23/24/25-45-41-37/38-20/21/22-48/23-38-67-37
Signal word
Danger
Symbol(GHS)
GHS05,GHS08
hazard_code
Xn,T,Xi
hazard_note
Harmful
safety_code
26-45-37/39-24-22-36/37-24/25-23-53-36-63-39
hazard_class
9
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
target organs
Lungs
Hazard statements
H315-H318-H372
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation
Autoignition Temperature
570 °C
Precautionary statements
P280-P302+P352-P305+P351+P338+P310-P314

Chemistry & industry

Pharmacology

Tissue LocationsBladder
Cellular LocationsCytoplasm
Applications · 7 items

Uses1. Used as a chemical reagent and preservative. 2. Benzoic acid is important type food preservative. Under acidic conditions, It has inhibitory effects to mold, yeast and bacteria , but the effect is weak acid producing bacteria. The most appropriate antimicrobial pH values is ranging from 2.5 to 4, generally lower, the pH value is appropriate from 4.5 to 5. In the food industry with plastic barrels concentrated fruit and vegetable juice, the maximum use amount shall not be over 2.0g/kg; in jam (excluding canned), (taste) juice drink, soy sauce, vinegar in the maximum dose of 1.0g/kg; in soft candy, wine, wine in the maximum dose of 0.8 g/kg separately; in the low salt pickled vegetables, the sauce, candied fruit, maximum dose is 0.5 g/kg; in carbonated drinks in the largest amount of use is 0.2g/kg. due to benzoic acid, slightly soluble in water, its use can be a small amount of ethanol enable dissolved. 3.Preservative; anti microbial agents. Due to the low solubility of benzoic acid and use shall be stirring, or dissolved in a small amount of hot water or ethanol. When used in the soft drink with fruit juice concentrate, for benzoic acid easy volatile with the water vapor, so often used in the sodium salt, besides the above sodium equivalent to benzoic acid 0.847g. 4.Often used as a fixative agent or preservative. Also used as a fruit juice aroma conservation agents. As a perfume with perfume fragrance. Can also be used for chocolate, lemon, orange, berries, nuts, candied fruit type edible essence. Tobacco flavor is also commonly used. 5.Benzoic acid and its sodium salt are food preservatives. Under acidic conditions, it has inhibition of yeasts and molds. When pH 3, antibacterial strength and when pH 6, many fungi effect is very poor, so the antibacterial optimum pH is 2.5-4.0. Benzoic acid is mainly used for the production of sodium benzoate preservatives, dyes intermediates, pesticides, plasticizers, mordant, medicine, spice and also can be used as alkyd resin and polyamide resin modifier for the production of polyester, terephthalic acid and used equipment, iron and steel anti rust agent. 6.Mainly used for antifungal and antiseptic. 7.Used in medicine, dye carriers, plasticizer, spices and food preservatives such as production, and can also be used to paint of alkyd resin performance improvement; used as pharmaceutical and dye intermediates, used for the preparation of plasticizer and spices etc., as well as equipment, iron and steel anti rust agent.

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Compound notes

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FLAVIS Number
8.021 · 08.021 | Benzoic acid
Flash point
250 °F · 250 °F
storage temp.
2 · 2-8°C
solubility
soluble, clear, colorless (95% ethanol, 1gm/3mL)
form
Solid
pka
4.19 · 4.19(at 25℃)
color
White to yellow-beige to orange
PH
3.66 · 3.66(1 mM solution);3.12(10 mM solution);2.6(100 mM solution);
Odor
100 % · at 100.00 %. faint balsam urine
Odor Type
balsamic
biological source
synthetic
Water Solubility
0.34 g/100 · Slightly soluble. 0.34 g/100 mL
Specific Heat Capacity
1.2 J/ · Cp(crystal): 1.2 J/(g·K), at 25℃
JECFA Number
850 · 850
Merck
14 · 14,1091
BRN
636131 · 636131
Henry's Law Constant
(x 10-8 atmm3/mol): 7.02 (calculated, U.S. EPA, 1980a)
Stability
Stable. Combustible. Incompatible with strong bases, strong oxidizing agents, alkalies.
Cosmetics Ingredients Functions
pH ADJUSTERSPRESERVATIVEFRAGRANCE
Cosmetic Ingredient Review (CIR)
Benzoic acid (65-85-0)
InChI
1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChIKey
WPYMKLBDIGXBTP-UHFFFAOYSA-N
SMILES
OC(=O)c1ccccc1
LogP
1.87 · 1.870
CAS DataBase Reference
65 · 65-85-0(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
BENZOIC ACID
FDA 21 CFR
175.3 · 175.300; 177.1390
SCOGS (Select Committee on GRAS Substances)
Benzoic Acid
EWG's Food Scores
1 · 1-3
FDA UNII
8 SKN0B0MIM · 8SKN0B0MIM
NIST Chemistry Reference
Benzoic acid(65-85-0)
EPA Substance Registry System
Benzoic acid (65-85-0)
UNSPSC Code
77101502 · 77101502
NACRES
24 · NA.24
Symbol(GHS)
5 · GHS05,GHS08
Signal word
Danger
Hazard statements
315 · H315-H318-H372
Precautionary statements
280 · P280-P302+P352-P305+P351+P338+P310-P314
target organs
Lungs
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn,T,Xi
Risk Statements
22 · 22-36-42/43-36/37/38-40-63-43-23/24/25-45-41-37/38-20/21/22-48/23-38-67-37
Safety Statements
26 · 26-45-37/39-24-22-36/37-24/25-23-53-36-63-39
RIDADR
3077 · UN 3077 9/PG 3
WGK Germany
1 · 1
RTECS
875000 · DG0875000
F
21 · 21
Autoignition Temperature
570 °C · 570 °C
Hazard Note
Harmful
TSCA
TSCA listed
HS Code
2916 · 2916 31 00
HazardClass
9 · 9
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
1 Skin · Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation
Hazardous Substances Data
65 · 65-85-0(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 1700 mg/kg LD50 dermal Rabbit > 5000 mg/kg
REACH Registrations
Active
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazardous Substances Data
65-85-0(Hazardous Substances Data)

DescriptionBenzoic acid is a colorless, crystalline solid also known as benzenecarboxylic acid. It is the simplest aromatic carboxylic acid, with a carboxyl group (-COOH) bonded directly to the benzene ring. It is found naturally in the benzoin resin of a number of plants.

OccurrenceReported found in fresh apple, apricot (Prunus armeniaca L.), strawberry fruit, cherry (Prunus cerasus L.), butter, boiled and cooked beef, pork fat, white wine, black tea, green tea, fresh plum, mushroom, Bourbon vanilla (Vanilla planifolia Andrews), and other natural sources. Reported as being a constituent of various oils, resins and flower absolutes; hyacinth, tuberose, neroli bigarade, Chinese cinnamon, cinnamon leaves, anise, vertiver, ylang-ylang, Tolu balsam and clove; it is contained in fairly sizable amounts in gum benzoin, from which benzoic acid is extracted by sublimation.

HistoryBenzoic acid was first isolated from the dry distillation of benzoin by Blaise de Vigenère (1523–1596) in the 16th century. Friedrich Whler (1800–1882) and Justus von Liebig (1803–1873) prepared benzoic acid from oxidizing bitter almond oil (benzaldehyde) in 1832 and determined the formula for each of these compounds. They proposed that bitter almond oil, C7H6O, and benzoic acid were derivatives from the benzoyl radical, C7H5O; the radical theory was a major early theory in the development of organic chemistry.

UsesCalorimetry Benzoic acid is the most commonly used chemical standard to determine the heat of capacity of a bomb calorimeter. Feed stock Benzoic acid is used to make a large number of chemicals, important examples of which are : Benzoyl chloride, C6H5C(O)Cl, is obtained by treatment of benzoic with thionyl chloride, phosgene or one of the chlorides of phosphorus. C6H5C(O) Cl is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used in artificial flavours and insect repellents. Food preservative Benzoic acid and its salts are used as a food preservatives, represented by the E-numbers E210 , E211 , E212 , and E213 . Benzoic acid inhibits the growth of mold, yeast and some bacteria. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. The mechanism starts with the absorption of benzoic acid in to the cell. Medicinal Benzoic acid is a constituent of Whitfiel's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot. As the principal component of benzoin resin, benzoic acid is also a major ingredient in both tincture of benzoin and Fria's balsam. Such products have a long history of use as topical antiseptics and inhalant decongestants. Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.

UsesSodium benzoate is an important benzoic acid derivative produced industrially by neutralization of benzoic acid using sodium hydroxide or sodium bicarbonate solution. Calcium benzoate, potassium benzoate, and other benzoate salts are also produced. Benzoic acid and sodium benzoate (C6H5COONa) are used as food preservatives and added to foods, juices, and beverages that are acidic.

General DescriptionBoric acid,H3B03, also known as boracic acid, orthoboric acid, and sassolite, is a white solid composed of triclinic crystals.It is a derivative of barium oxide and is soluble in water. A white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses.

Preparation methods · 2 items

PreparationIndustrial preparation method The industrial benzoic acid is mainly by toluene liquid phase air oxidation preparation. The process was with cobalt naphthenate as catalyst, in response to temperature is 140-160 ℃ and operating pressure is 0.2-0.3MPa and response generation benzoic acid. Reaction after steaming to toluene, and vacuum distillation and recrystallization to obtain the product. The process uses cheap raw materials, high yield. Therefore, it is industrial uses mainly the method. Laboratory preparation method of the main reaction: 1.C6H5CH3+ KMnO4+H2O-C6H5 COOK+KOH+MnO2+H2O(water in fron of the manganese dioxide is supplied with water reaction environment) 2.C6H5 COOK+HCl--C6H5 COOH Drug and dosage: Toluene 1.5g (1.7ml, 0.016mol), potassium permanganate 5g (0.032mol), CTAB(cetyl trimethyl ammonium bromide) 0.1g. Experimental operation: With 100 ml round bottom flask. Install a refluxing device. add 5g potassium permanganate, 0.1g of hexadecyl trimethyl ammonium bromide, 1.7 ml of toluene and 50 ml of water to the reaction flask, stir heated boiling (vigorous stirring, violent boiling), keep the reactant solution stable boiling. When large amounts of brown precipitate, potassium permanganate purple shallow or disappeared, the toluene layer disappeared, reaction has basically ended. Filter out of manganese dioxide precipitation, landfill leachate by concentrated hydrochloric acid, precipitation of benzoic acid precipitation, filtering to the crude product. The crude product water recrystallization. In a boiling water bath for drying, weighing, measuring the melting point.

PreparationBy oxidation of toluene with nitric acid or sodium bichromate or from benzonitrile.

Upstream & downstream products

Upstream raw materials

Hippuric acidCobalt acetateNaphthaleneArsenicBenzyl alcoholZinc oxideLead monoxideTolueneChlorineFormic acidPhthalic acidBenzotrichlorideCobalt naphthenatePhthalic anhydride

Downstream products

(S)-(-)-N-Benzyl-1-phenylethylamineEthyl 3,4-dihydroxybenzoateBenzoyl peroxideSodium benzoate3-Nitrobenzoic acid4-tert-Butylphenol2,5-Diphenyl-1,3,4-oxadiazole3-Methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene2-Iodoxybenzoic acidPhenolic resin paintDirect Yellow 123,5-Diaminobenzoic acid3-Hydroxybenzoic acidAmmonium benzoateIsoamyl benzoate2-MethylbenzanilideExemestaneDirect Black 168MCBEAmino resin paint3,5-Dihydroxybenzoic acidMethyl benzoate3-Sulfamoyl-benzoic acidChorionic GonadotropinMethyl acrylateFluorescamineBenzoyl chlorideBenzyl benzoatePotassium benzoate
Additional notes · 1 item

DefinitionChEBI: Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate.