3-Hydroxy-2-naphthoic acid

log Kow = 3.05

3.4-3.59

Very pale yellow crystals

Yellow rhombic leaflets

Sol in benzene, chloroform, alkaline soln; freely soluble in alcohol and ether

SOL IN TOLUENE

0.1 wt% in water at 25 °C

Solubility in water, g/100ml: 0.047 (very poor)

222-223 °C

Lemon to greenish yellow, odorless powder, MP: 218 °C (minimum) /Commercial product, 98% purity/

220 °C

0.00000054 [mmHg]

Vapor pressure, Pa at 25 °C: (negligible)

Dry Powder; CBI

Pale yellow solid; [Merck Index] Pale yellow crystalline solid; [MSDSonline]

YELLOW CRYSTALS.

This chemical does not meet GHS hazard criteria for 0.5% (1 of 209) of reports.

Danger

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 209 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: 2-Naphthalenecarboxylic acid, 3-hydroxy-

2-Naphthalenecarboxylic acid, 3-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenecarboxylic acid, 3-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 21-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14175

3-Hydroxy-naphthalene-2-carboxylic acid: Does not have an individual approval but may be used under an appropriate group standard

Emergency medical treatment: irritants; [HSDB] Cause severe damage to eyes in animal studies; Causes skin necrosis after occlusive exposure for 24 hours to the 10-12% solution; Positive for sensitization in a guinea pig maximization test after open epicutaneous challenge. Negative results in patch testing 36 humans volunteers; Evidence of liver and kidney injury in high-dose animal studies; [OECD SIDS: 3-Hydroxy-2-naphthoic acid - 2004] An irritant; [MSDSonline]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3-Hydroxy-2-naphthoic acid is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Acute Tox. 4 (99.5%)

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a measured log Kow of 3.05(2) and a regression-derived equation(3), indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to have low mobility in soil(SRC). The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), which indicates that this compound will exist primarily as an anion in moist soil and the mobility of anions is usually much greater than neutral species(5). Volatilization of 3-hydroxy-2-naphthalenecarboxylic acid from moist soil surfaces is not expected to be an important fate process since anions do not volatilize. 3-Hydroxy-2-naphthalenecarboxylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-7 mm Hg(SRC), determined from a fragment constant method(6). The results of a single screening study using an activated sludge inoculum(7) suggest that 3-hydroxy-2-naphthalenecarboxylic acid is biodegraded slowly in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a measured log Kow of 3.05(2) and a regression-derived equation(3), indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to adsorb to suspended solids and sediment(SRC). The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), which indicates that this compound will exist primarily as an anion in water and may not absorb to suspended solids and sediments as much as the neutral species (SRC). Volatilization from water surfaces is not expected to be an important environmental fate process since anions do not volatilize(SRC). According to a classification scheme(5), BCF values of 6.7 or lower measured in carp(6), suggest bioconcentration in aquatic organisms is low(SRC). A 1.3% of its theoretical BOD in 2 weeks using an activated sludge inoculum and the Japanese MITI test(6) suggests that 3-hydroxy-2-naphthalenecarboxylic acid is biodegraded slowly in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-hydroxy-2-naphthalenecarboxylic acid, which has an estimated vapor pressure of 5.4X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-hydroxy-2-naphthalenecarboxylic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 hours(SRC), calculated from its rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase 3-hydroxy-2-naphthalenecarboxylic acid may be removed from the air by wet and dry deposition(SRC). 3-Hydroxy-2-naphthalenecarboxylic acid absorbs light in the environmental UV spectrum(4) and may be capable of undergoing photolysis, but the rate of this reaction is not known(SRC).

Sore throat. Cough.

Redness. Pain.

Redness. Pain. Burns.

Sore throat. Nausea. Vomiting. Diarrhoea.

The Koc of 3-hydroxy-2-naphthalenecarboxylic acid is estimated as 1,100(SRC), using a measured log Kow of 3.05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-hydroxy-2-naphthalenecarboxylic acid is expected to have low mobility in soil. The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), indicating that this compound will exist as an anion in moist soils(SRC) and the mobility of anions is usually much greater than neutral species(5).

THE BIODEGRADABILITY OF ORG SUBSTANCES IN WASTEWATER BY ACTIVATED-SLUDGE WAS DETERMINED. BETA-HYDROXYNAPHTHOIC ACID WAS RESISTANT TO DEGRADATION.

3-Hydroxy-2-naphthalenecarboxylic acid, present at 100 mg/l, reached 1.3% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1).

The BCF values of 3-hydroxy-2-naphthalenecarboxylic acid at water concentrations of 0.1 and 1.0 mg/l were 6.7 or lower, measured in carp over an 6 week exposure period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for 3-hydroxy-2-naphthalenecarboxylic acid is estimated as 1.4X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to be essentially nonvolatile from water surfaces(2). Furthermore, 3-hydroxy-2-naphthalenecarboxylic acid is a weak acid with pKa of 2.79(2), indicating that this compound will exist as an anion in the environment, and anions do not volatilize from water or soil surfaces(SRC). 3-Hydroxy-2-naphthalenecarboxylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-7 mm Hg(SRC), determined from a fragment constant method(4).

/LABORATORY ANIMALS: Acute Exposure/ ... Irritating to rabbit eyes but not to rabbit skin. /Commercial product, 98% purity/

/LABORATORY ANIMALS: Acute Exposure/ Acute effects on skin: moderate irritant on guinea pig skin, not sensitizer. /from table/

/ALTERNATIVE IN VITRO TESTS/ In rat liver mitochondrial preparations in the absence of phosphate acceptor, uncoupling activities for beta-hydroxynaphthoic acid was greater than that of salicylic acid.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3-Hydroxy-2-naphthoic acid is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Used as a chemical intermediate for dyes and pigments; Has been used as a gallbladder stimulant; [HSDB] Used as intermediate for insecticides and pharmaceuticals; [eChemPortal: SIDSUNEP]

DYES & PIGMENTS

CHEM INT FOR DYES-EG, PIGMENT REDS 57:1, 52:1, 48:2, 48:1

CHEM INT FOR P-(NAPHTHYLAMINO)PHENOL-INT FOR SULFUR DYES

MEDICATION

(1979) 5.99X10+8 G (PRINCIPAL CUSTOMS DISTRICTS)

(1981) 5.04X10+8 G (PRINCIPAL CUSTOMS DISTRICTS)

2023: 1,000,000 - <8,500,000 lb

(1977) AT LEAST 4.54X10+8 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Synthetic Dye and Pigment Manufacturing

2-Naphthalenecarboxylic acid, 3-hydroxy-: ACTIVE

Absorption of polar bioactive substances from the GI tract is enhanced by including a hydroxyaromatic acid adjuvant in the formulation.

Hydroxyaryl acids incorporated into suppositories to enhance the absorption rate of the rectally delivered drugs. /Hydroxylaryl acids/

Oral formulatons for improved absorption of beta-lactam antibiotics such as penicillins, cephalosporins, etc, comprise hydroxyaryl acids as adjuvants.