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3, 5-dihydroxybenzoic acid is a metabolite of alkylresinols with a certain activation effect on HCA1. It can be used as intermediates in organic synthesis.
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Commey, Leslie ; Mechref, Yehia ; Burow, Mark ; Mendu, Venugopal ;
Abstract: The peanut seed coat acts as a physical and biochemical barrier against Aspergillus flavus infection; however, the nature of the inhibitory chemicals in the peanut seed coat in general is not known. This study identified and characterized peanut seed coat metabolites that inhibit A. flavus growth and aflatoxin contamination. Selected peanut accessions grown under well-watered and water-deficit conditions were assayed for A. flavus resistance, and seed coats were metabolically profiled using liquid chromatography mass spectrometry. Kyoto Encyclopedia of Genes and Genome phenylpropanoid pathway reference analysis resulted in the identification of several seed coat metabolic compounds, and ten selected metabolites were tested for inhibition of A.flavus growth and aflatoxin contamination. Radial growth bioassay demonstrated that 2,5-dihydroxybenzaldehyde inhibited A. flavus growth (98.7%) and reduced the aflatoxin contamination estimate from 994 to 1 μg/kg. Scanning electron micrographs showed distorted hyphae and conidiophores in cultures of 2,5-dihydroxybenzaldehyde-treated A. flavus, indicating its potential use for field application as well as seed coat metabolic engineering.
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Keywords: aflatoxin, A. flavus ; metabolomics ; seed coat ; liquid chromatography mass spectrometry (LC-MS) ; radial growth bioassay ; secondary metabolites
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CAS No. : | 99-10-5 |
Formula : | C7H6O4 |
M.W : | 154.12 |
SMILES Code : | O=C(O)C1=CC(O)=CC(O)=C1 |
MDL No. : | MFCD00002512 |
InChI Key : | UYEMGAFJOZZIFP-UHFFFAOYSA-N |
Pubchem ID : | 7424 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine; at 90 - 100℃; for 0.166667h; | A mixture of 7.7 g (0.05 mol) of 3,5-dihydroxybenzoic acid (1), 25 mL of acetic anhydride and 2 mL of triethylamine was mixed and stirred for 10 min and heated at 90 to 100 C. TLC was monitored. Product into the ice water, a large number of white precipitate generated, filtered to obtain a white solid is the crude product,Recrystallization from ethanol gave 11.0 g of white crystals (2) in 92% yield. |
91% | at 130℃; for 4h; | General procedure: Garlic acid (2000 mg, 11.763 mmol) was dissolved in acetic anhydride(7205 mg, 70.578 mmol). The solution was then heatedunder reflux at 130 C for 4 h, after which the deionized water(4 ml) was add to the solution to remove the unreacted acetic anhydride.The solvent was removed using a rotary evaporator underreduced pressure to yield white solid. The product was recrystallizedin CH2Cl2 and dried under vacuum. Yielding 95% compound 4a(3308 mg) as a white solid. Compounds 4b-c were synthesizedfollowing the procedure of preparation 4a. |
90% | Preparation of 3,5-diacetyloxybezoic acid: Reaction Scheme 1-iTo 200 ml of tetrahydrofuran, 15.4 g (0.09 mol) of 3,5-dihydroxybenzoic acid and 38 ml (0.27 mol) of triethylamine were added, and the reaction mixture was stirred for 10 minutes. To the reaction mixture, 23 ml (0.24 mol) of acetic anhydride was added dropwise, and then the resultant mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and allowed to evaporate under reduced pressure. Then, dichloromethane and water were added thereto, and the organic layer was washed with water and 1N aqueous HCl solution many times, and allowed to evaporate under reduced pressure. Hexane was added to the remaining oil to form precipitate. The precipitate was filtered under reduced pressure to obtain 15 g (90%) of the target product. |
90% | [Example 1] Preparation of 3,5-dihydroxy-N-(4-hydroxyphenyl)benzamide; Preparation of 3,5-diacetyloxybezoic acid:; Reaction Scheme l-i>To 200ml of tetrahydrofuran, 15.4g (0.09mol) of 3,5-dihydroxybenzoic acid and 38ml (0.27mol) of triethylamine were added, and the reaction mixture was stirred for 10 minutes. To the reaction mixture, 23ml (0.24mol) of acetic anhydride was added dropwise, and then the resultant mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and allowed to evaporate under reduced pressure. Then, dichloromethane and water were added thereto, and the organic layer was washed with water and IN aqueous HCl solution many times, and allowed to evaporate under reduced pressure. Hexane was added to the remaining oil to form precipitate. The precipitate was filtered under reduced pressure to obtain 15g (90%) of the target product. | |
88.4% | With pyridine; at 100℃; | Step 1: Acetoxybenzoic Acid A 100 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 30 g (0.195 mol) of 3,5-dihydroxybenzoic acid, 47 ml (0.497 mol) of acetic anhydride and 2.4 ml (29.8 mmol) of pyridine. The mixture was heated to 100 C. and kept under stirring for 3-4 hours then cooled down, poured into 400 ml of ice water and filtered. The filter cake was washed with ice water and dried at 45 C. under 1 mbar vacuum. 41 g of 3,5-diacetoxybenzoic acid as a white solid was obtained. The yield was 88.4%. |
88.4% | With pyridine; at 100℃; | Step 1: Acetoxybenzoic acid A 100 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 30 g (0.195 mol) of 3,5-dihydroxybenzoic acid, 47ml (0.497 mol) of acetic anhydride and 2.4 ml (29.8 mmol) of pyridine. The mixture was heated to 100 C and kept under stirring for 3 to 4 hours then cooled down, poured into 400 ml of ice water and filtered. The filter cake was washed with ice water and dried at 45 C under 1 mbar vacuum. 41 g of 3,5-diacetoxybenzoic acid as a white solid was obtained. The yield was 88.4 %. |
72% | With pyridine; dmap; In ethyl acetate; at 0 - 20℃; | A suspension of 3,5-dihydroxybenzoic acid (15.40 g, 0.100 mol) in ethyl acetate (220 mL) wascooled in an ice-bath. Acetic anhydride (24.52 mL, 0.2421 mol), pyridine (16.16 mL, 0.1998 mol) and4-(dimethylamino)pyridine (100 mg, 0.8186 mmol) were added and the reaction stirred at 0 C for60 min and then at room temperature overnight. Formic acid (5.12 mL, 0.1357 mmol) was added andthe reaction poured onto ice (ca. 500 g). The volume was increased by the addition of further ethylacetate (300 mL) and the organic phase separated and washed with water (2 × 200 mL), sat. aq. NaHCO3(100 mL), further water (2 × 200 mL), and then dried and evaporated to a white solid. Recrystallization ofthe product from 5:1 (v/v) EtOAc/hexane (120 mL) gave 2 crops of 3,5-diacetoxybenzoic acid (combinedweight 17.07 g, 72%) as a white powder. Rf 0.20 (1:1 EtOAc/hexane), 0.39 (3:1 EtOAc/hexane); mp161-162 C (lit. [27] mp: 157-159 C); δH (CDCl3) 2.29 (s, 6H, 2 × OAc), 7.18 (pseudo t, 1H,J = 2.1 Hz, 4-H) and 7.70 (pseudo d, 2H, J = 2.1 Hz, 2-H, 6-H); δC (CD3OD) 18.43, 118.94, 119.02,131.70, 150.19, 165.46 and 168.17; m/z (ESI) 261 ([M + Na]+, 100%). |
34% | for 6h;Reflux; | A 500 mL round bottom flask was charged with 3,5-dihydroxybenzoic acid (77.00 g,0.50 mol) and acetic anhydride (200 mL). The reaction mixture was heated to reflux, asthe temperature increased the dihydroxy acid gradually dissolved into solution and themixture was left to reflux for 6 h. A brown solution was obtained containing a small amountof insoluble material; the excess acetic anhydride and acetic acid by-product were removedunder reduced pressure, the compound dissolved in refluxing chloroform (200 mL) andfiltered hot. Petroleum ether (70 mL) was then added to the mother liquor, precipitating awhite solid. The mixture was left overnight, and a white product was isolated by filtration,which was thoroughly washed with petroleum ether. Yield: 40.60 g, 34%; 1H NMR (CDCl3) 10.19 (br s, 1H, -COOH), 7.76 (d, 2H, Ar o-CH), 7.22 (t, 1H, Ar p-CH), 2.31 (s, 6H, -CH3);13C NMR (CDCl3, 300 MHz) 170.0 (COOH), 168.8 (C=O), 151.3 (m-Ar), 131.4 (i-Ar), 122.1(p-Ar), 121.0 (o-Ar), 21.0 (CH3); IR (cm1) 3400-2400, 1765 (COOR), 1687 (COOH), 1603;ES-MS, 237 (M+); MP 160-162 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | EXAMPLE 2 Preparation of 3,5-Diacetoxybenzoic Acid from 3,5-Dihydroxybenzoic Acid (Branching Monomer) 3,5-Dihydroxybenzoic acid (446.42 g, 2.89 moles) was charged to a 2000 mL round bottom 3-neck flask with a Friedrich condenser and thermocouple under a blanket of nitrogen. Acetic arkhydride (1515 g, 14.85 moles) was added slowly. The suspension was stirred and refiuxed (-135 C.) for 3 hours. After cooling, the cream solid was filtered off and washed with toluene. The acetic anhydride was removed under reduced pressure 2 more times to yield additional cream solids. Yield of 3,5-diacetoxybenzoic acid (347.02 g, 50%, HPLC 97.5% purity). DSC m.p. 155 C. 1H NMR (400 MHz, d6 -DMSO) δ 13.31, 7.59, 7.28, 2.29. 13C NMR (100 MHz, d6 -DMSO)δ 169.20, 166.01, 151.15, 133.12, 120.53, 120.32, 20.70 MS (DIP) m/e 238 (M+). | |
50% | With acetic anhydride; | EXAMPLE 2 Preparation of 3.5-Diacetoxybenzoic Acid from 3.5-Dihydroxybenzoic Acid (Branching Monomer) 3,5-Dihydroxybenzoic acid (446.42 g, 2.89 moles) was charged to a 2000 mL round bottom 3-neck flask with a Friedrich condenser and thermocouple under a blanket of nitrogen. Acetic anhydride (1515 g, 14.85 moles) was added slowly. The suspension was stirred and refluxed (~ 135 C.) for 3 hours. After cooling, the cream solid was filtered off and washed with toluene. The acetic anhydride was removed under reduced pressure 2 more times to yield additional cream solids. Yield of 3,5-diacetoxybenzoic acid (347.02 g, 50%, HPLC 97.5% purity). DSC m.p. 155 C. 1H NMR (400 MHz, d6 -DMSO) δ 13.31, 7.59, 7.28, 2.29. 13C NMR (100 MHz, d6 -DMSO)δ 169.20, 166.01, 151.15, 133.12, 120.53, 120.32, 20.70 MS (DIP) m/e 238 (M+). |
With hydrogenchloride; sulfuric acid; In acetic anhydride; | EXAMPLE 7 6-Amino-5-(3,5-diacetoxyphenyl)carboxyamido-3-methyl-1-phenyluracil 3,5-Dihydroxybenzoic acid (7.2 g, 50 mM) was dissolved in 11 ml of acetic anhydride. To the resulting solution were added 5 drops of sulfuric acid, followed by stirring at room temperature for 20 minutes. Subsequently, 10 g of ice was added and 12 ml of 1N hydrochloric acid was then added. After sonication, a precipitated crystal was recovered by filtration. Washing the crystal with toluene gave 3,5-diacetoxybenzoic acid (10.23 g). |
With pyridine; formic acid; acetic anhydride; In ethyl acetate; | Example 10 3,5-Diacetoxybenzoic acid (10). A suspension of 3,5-dihydroxybenzoic acid in ethyl acetate was cooled in an ice-bath. Acetic anhydride and pyridine were added and the reaction allowed proceeding for 60 minutes. The homogenous solution was stirred overnight at room temperature. Formic acid was added and the solution then poured onto ice-water. Further ethyl acetate was added and the organic phase separated and successively washed twice each with sat. NaHCO3 and water, then dried, filtered and rotary evaporated to give a white solid. Recrystallization from EtOAc/hexane produced 3,5-diacetoxybenzoic acid as a white powder. Rf 0.20 (1:1 hexane/EtOAc), 0.39 (3:1 hexane/EtOAc); mp 161-162 C., lit mp: 157-159 C. Turner et al, Macromolecules, 1993, 26, 4617-4623; 1H NMR (CDCl3): δ 2.29 (s, 6H, 2*OAc), 7.18 (pseudo t, 1H, J=2.1 Hz, H4), 7.70 (pseudo d, 2H, J=2.1 Hz, H2, H6); 13C JMOD NMR (CD3OD): δ 18.43 (2*CH3), 118.94 (C4), 119.02 (C2,6), 131.70 (C1), 150.19 (C5), 165.46 (COOH), 168.17 (2*OCOCH3); LRESI positive ion mass spectrum; m/z 261 (MNa+, 100%). | |
With pyridine; dmap; formic acid; acetic anhydride; sodium hydrogencarbonate; In water; ethyl acetate; | 3,5-Diacetoxybenzoic acid A suspension of 3,5-dihydroxybenzoic acid (15.40 g, 0.100 mol) in ethyl acetate (220 mL) was cooled in an ice-bath. Acetic anhydride (24.52 mL, 0.2421 mol), pyridine (16.16 mL, 0.1998 mol) and 4-(dimethylamino)pyridine (100 mg, 0.81855 mmol) were added and the reaction stirred at 0 C. for 60 minutes and then at room temperature overnight. Formic acid (5.12 mL, 0.1357 mmol) was added and the reaction poured onto ice (ca. 500 g). Further ethyl acetate (300 mL) was added and the organic phase separated and washed with water (2*200 mL), sat. aq. NaHCO3 (100 mL), further water (2*200 mL), and then dried and evaporated to a white solid. Recrystallization from 5:1 EtOAc/hexane (120 mL) gave 2 crops of 3,5-diacetoxybenzoic acid (combined weight 17.07 g, 72%) as a white powder. Rf 0.20 (1:1 EtOAc/hexane), 0.39 (3:1 EtOAc/hexane); mp 161-162 C. (from EtOAc/hexane) (lit. mp: 157-159 C.); δH(CDCl3) 2.29 (s, 6H, 2*OAc), 7.18 (pseudo t, 1H, J 2.1, 4-H) and 7.70 (pseudo d, 2H, J 2.1, 2-H, 6-H); δC(CD3OD) 18.43, 118.94, 119.02, 131.70, 150.19, 165.46 and 168.17; m/z (ESI) 261 (MNa+, 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetic anhydride; | The starting material can be manufactured, for example, as follows: 50 g of 3,5-dihydroxybenzoic acid are suspended in 132.2 g of acetic anhydride and heated to 50. After the addition of 15 drops of concentrated H2 SO4, the resulting solution is stirred for 1 hour at 60. The reaction mixture is poured onto ice and extracted with CH2 Cl2. The combined organic phases are washed 3 times with H2 O, dried over Na2 SO4 and concentrated by evaporation. The residue is crystallized from ether and yields 3,5-diacetoxybenzoic acid having a melting point of 140-145. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; acetic anhydride; In pyridine; CH2 Cl; 5,5-dimethyl-1,3-cyclohexadiene; hydrogen; benzene; | EXAMPLE 1 3,5-Diacetoxybenzaldehyde A total of 82.4 ml of acetic anhydride (89.8 g, 0.88 mole) was added in small portions to a stirring mixture of 61.7 g of 3,5-dihydroxybenzoic acid (0.4 mole) in 130 ml of pyridine. After the addition was complete, the reaction mixture was left stirring for 15 hours at ambient temperature. The pyridine was removed by evaporation in vacuo. The residue was taken up in CH2 Cl 2 and washed several times with 6N HCl and water and dried (Na2 SO4). Removal of solvent under reduced pressure left 68.2 g (72%) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> which was used without further purification. A stirring mixture of 68.2 g (0.29 mole) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> and 21 ml (0.29 mole) of thionyl chloride in 150 ml of dry benzene was heated in an oil bath at 80-90 C. for 2 hours. After cooling the benzene was removed in vacuo to leave 3,5-diacetoxybenzoyl chloride as a tan, solid which was recrystallized from cyclohexane as colorless crystals, mp 87-89 C., 61.8 g (83% yield). A mixture of 61.8 g (0.24 mole) of 3,5-diacetoxybenzoyl chloride and 6 g of 5% palladium on BaSO4 in 200 ml of dry xylene was efficiently stirred while bubbling in hydrogen gas. The reaction mixture was slowly heated to 115 C. in an oil bath and the heating was continued until the evolution of HCl gas ceased (approximately 5 hours). After cooling, the mixture was filtered and the xylene was removed in vacuo to leave 48 g (90%) of 3,5-diacetoxybenzaldehyde which was used without further purification in subsequent reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.3% | 5. Preparation of 3,5-diacetoxybenzoic acid To a solution of 3,5-dihydroxybenzoic acid (7.71 g, 50 mmol) in EtOAc (10 mL) were added acetic anhydride (12.25 mL, 130 mmol) and pyridine (8.08 mL, 100 mmol) in an ice-water bath under a nitrogen atmosphere. The mixture was stirred at 0 C. for 40 min and then stirred at ambient temperature for 4 h. 98% Formic acid (2.36 mL, 60 mmol) was added and the resulting mixture was stirred for 1 h. Then, it was poured into water and extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and evaporated in vacuo. Purification of the residue via recrystallization from n-heptane/EtOAc provided 3,5-diacetoxybenzoic acid (8.97 g, 75.3%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 12.1 (bs, 1H), 7.73 (d, 2H), 7.21 (t, 1H), 2.32 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 170.4, 169.0, 151.2, 131.5, 121.3, 121.0, 21.2; mp=161-162 C.; HRMS (EI+) found 238.0475 M+, calcd 238.0477 for C11H10O6; Anal. Calcd for C11H10O6: C, 55.47; H, 4.23. Found: C, 55.62; H, 4.37. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In methanol; water; for 0.5h; | 2.2.1 Synthesis of [(C4H8N5+)·(C7H5O4-)]·2H2O hydrous salt (1) The <strong>[1004-38-2]TAP</strong>I (0.20 mmol) and HDHBA (0.40 mmol) were dissolved in 10 ml of methanol-distilled water (H2O) mixed solution. The mixed solution was stirred for 30 min to receive a colorless solution. After seven days of slow evaporation, crystals with good diffraction quality were obtained at 20-25 C. The resulting crystals were filtered and dried after rinsed with methanol-H2O mixed solution. Yield: 62%. Analysis calculated for C11H17N5O6: C, 41.85; H, 5.39; N, 22.20%. Found: C, 42.11; H, 5.42; N, 22.31%. Infrared spectrum (KBr disc, cm-1): 3429s, 3375s, 3315s, 3192s, 1683s, 1635s, 1610s, 1583s, 1516s, 1481m, 1424s, 1331m, 1303m, 1267m, 1245m, 1200w, 1163m, 1103w, 1007m, 982w, 940m, 920w, 853w, 871w, 797m, 767m, 730m, 698m, 665m, 470m. |
Tags: 3,5-Dihydroxybenzoic acid | Carboxylic Acids | Aryls | Phenols | GPCR | Organic Building Blocks | By Structure | Parkinson'S Disease and Alzheimer'S Disease | GPCR/G Protein | 99-10-5
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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