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487-54-7

Basic Information
CAS No.: 487-54-7
Name: 2-HYDROXYHIPPURIC ACID
Article Data: 10
Molecular Structure:
Molecular Structure of 487-54-7 (2-HYDROXYHIPPURIC ACID)
Formula: C9H9NO4
Molecular Weight: 195.175
Synonyms: Hippuricacid, o-hydroxy- (8CI);Salicyluric acid (6CI);(2-Hydroxybenzoyl)glycine;2-Hydroxyhippuric acid;N-(o-Hydroxybenzoyl)glycine;N-Salicyloylglycine;NSC524135;Salicyloylglycine;o-Hydroxyhippuric acid;
EINECS: 207-661-6
Density: 1.401 g/cm3
Melting Point: 164-169 °C
Boiling Point: 489.79 °C at 760 mmHg
Flash Point: 250.016 °C
Solubility: soluble in water
Appearance: light gray crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36/37/39-27-26
PSA: 86.63000
LogP: 0.59750
Synthetic route
178633-73-3

(2-Hydroxy-benzoylamino)-acetic acid benzyl ester

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol 0 deg C, then 0oom temp., overnight;92%
56-40-6

glycine

1441-87-8

salicyloyl chloride

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃;90%
With sodium hydroxide; water Erwaermen des nach dem Ansaeuern erhaltenen Reaktionsprodukts mit wss. Natronlauge;
27796-49-2

(2-methoxyphenyl)(methoxycarbonylmethylamino)-methanone

487-54-7

Salicyluric acid

Conditions
ConditionsYield
40%
64-17-5

ethanol

2-glycyloxy-benzoic acid ; perchlorate

487-54-7

Salicyluric acid

Conditions
ConditionsYield
at 20℃; Kinetics;
56145-98-3

N-salicyloyl-glycine amide

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With sodium hydroxide
856119-90-9

2-azidoacetoxy-benzoic acid

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With acetic acid methyl ester; platinum Hydrogenation;
With palladium on activated charcoal; acetic acid Hydrogenation;

2-(N-benzyloxycarbonyl-glycyloxy)-benzoic acid

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With palladium on activated charcoal; 2-methoxy-ethanol Hydrogenolyse;
116601-30-0

2-(N-benzyloxycarbonyl-glycyloxy)-benzoic acid benzyl ester

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With palladium on activated charcoal; 2-methoxy-ethanol Hydrogenolyse;
92505-60-7

2-methoxycarbonyloxy-benzoyl chloride

56-40-6

glycine

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With sodium hydroxide Behandeln des Reaktionsgemischs mit konz. Natronlauge;
54539-61-6

2-hydroxybenzoyl azide

56-40-6

glycine

487-54-7

Salicyluric acid

Conditions
ConditionsYield
With sodium hydroxide
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Specification

The Salicyluric acid with CAS registry number of 487-54-7 is also known as 2-Hydroxyhippuric acid. The IUPAC name is 2-[(2-Hydroxybenzoyl)amino]acetic acid. It belongs to product categories of Aromatics Compounds; Aromatics. Its EINECS registry number is 207-661-6. In addition, the formula is C9H9NO4 and the molecular weight is 195.17. This chemical is stable at normal temperature and pressure, and it should be sealed in a ventilated and dry place. What's more, it is a light gray crystalline powder.

Physical properties about Salicyluric acid are: (1)ACD/LogP: 0.81; (2)# of Rule of 5 Violations: 0 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 5; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.604; (11)Molar Refractivity: 47.955 cm3; (12)Molar Volume: 139.342 cm3; (13)Surface Tension: 65.897 dyne/cm; (14)Density: 1.401 g/cm3; (15)Flash Point: 250.016 °C; (16)Enthalpy of Vaporization: 79.642 kJ/mol; (17)Boiling Point: 489.79 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Salicyluric acid: it is prepared by reaction of (2-hydroxy-benzoylamino)-acetic acid benzyl ester. The reaction needs reagent H2, catalyst Pd/C and solvent methanol at the temperature of 0 °C over night. The yield is about 92%.

Salicyluric acid is prepared by reaction of (2-hydroxy-benzoylamino)-acetic acid benzyl ester.

Uses of Salicyluric acid: it is used to produce [(2-hydroxy-4,5-dioxo-4H,5H-pyrano[3,2-c]chromene-3-carbonyl)-amino]-acetic acid by reaction with propadienedione. The reaction occurs with solvent acetone at 0 °C for 5 hours and r.t. for 48 hours. The yield is about 70%.

Salicyluric acid is used to produce [(2-hydroxy-4,5-dioxo-4H,5H-pyrano[3,2-c]chromene-3-carbonyl)-amino]-acetic acid by reaction with propadienedione.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. After using it, take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C(=C1)C(=O)NCC(=O)O)O
2. InChI: InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
3. InChIKey: ONJSZLXSECQROL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD oral > 1gm/kg (1000mg/kg)   Farmaco, Edizione Scientifica. Vol. 30, Pg. 399, 1975.
mouse LDLo intravenous 600mg/kg (600mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: CHANGE IN RATE
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
pigeon LDLo intravenous 2080mg/kg (2080mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: CHANGE IN RATE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
pigeon LDLo subcutaneous 5730mg/kg (5730mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: CHANGE IN RATE
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.
rat LD50 subcutaneous 3gm/kg (3000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: CHANGE IN RATE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 38, Pg. 9, 1930.