*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
3-Hydroxyanthranilic acid is an intermediate in tryptophan metabolism via the kynurenine pathway, exhibiting antioxidant and anti-inflammatory properties. It regulates immune responses and plays a role in neuroprotection and immune regulation.
Synonyms: 3-HAA; NSC 522891
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 548-93-6 |
Formula : | C7H7NO3 |
M.W : | 153.14 |
SMILES Code : | C1=C(C(=C(C=C1)O)N)C(O)=O |
Synonyms : |
3-HAA; NSC 522891
|
MDL No. : | MFCD00007700 |
InChI Key : | WJXSWCUQABXPFS-UHFFFAOYSA-N |
Pubchem ID : | 86 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
With hydrogenchloride; In methanol; water; | Step 1 Methyl-2-amino-3-hydroxybenzoate To a solution of 2 g (13.1 mmol) of 2-amino-3-hydroxybenzoic acid in 60 mL of CH3OH at 0 C. was bubbled HCl gas until the solution was saturated. The reaction was heated at reflux for 12 h. The reaction mixture was concentrated and dissolved in 30 mL of water. The solution was neutralized with sat'd NaHCO3 solution and extracted with EtOAc. The organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to give 1.8 g of the title compound as a brown solid. | |
0.90 g (83%) | In methanol; | EXAMPLE 30 2-Amino-3-hydroxy-benzoic acid methyl ester To a solution of 1.0 g (6.53 mmol) of 3-hydroxyanthranilic acid in 15 mL of methanol was added 5.0 mL of BF3 -methanol complex and the resulting solution was heated to reflux for 24 h. After cooling to room temperatue the reaction mixture was poured into saturated sodium carbonate solution and then extracted with ether. The combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.90 g (83%) of the desired product as a brown solid. Electrospray Mass Spec: 167.8 (M+H)+ |
0.90g (83%) | In methanol; | Example 30 2-Amino-3-hydroxy-benzoic acid methyl ester To a solution of 1.0g (6.53mmol) of 3-hydroxyanthranilic acid in 15mL of methanol was added 5.0mL of BF3-methanol complex and the resulting solution was heated to reflux for 24h. After cooling to room temperature the reaction mixture was poured into saturated sodium carbonate solution and then extracted with ether. The combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.90g (83%) of the desired product as a brown solid. Electrospray Mass Spec: 167.8 (M+H)+ |
With thionyl chloride; In methanol; for 2h;Reflux; | To a solution of 2-amino-3-hydroxybenzoic acid (10 g, 65 mmol) in anhydrous methanol (300 mL) was added thionyl chloride (16 g, 0.13 mol) dropwise at room temperature. The solution was heated to reflux for 2 hours. On completion, the resulting solution was concentrated in vacuo to give compound B-257 (10 g, crude) as a red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; at 0℃;Reflux; | To a stirred solution of 2-amino-3-hydroxybenzoic acid (1.22 g, 8.0 mmol) in MeOH (80 mL) was added SOCI2 (9.52g, 80.0 mmol) dropwise at 0C. The mixture was then heated at reflux overnight. Most of the methanol was removed and the residue was partitioned between DCM and saturated aqueous NaHC03. The organic phase was washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure to give methyl 2-amino- 3-hydroxybenzoate (1.27 g, 95%). LC-MS (ES-API); rt 8.09 min; m/z calculated for C8H9N03 [M+H]+ 168.1, found 168.1. | |
With hydrogenchloride; toluene-4-sulfonic acid; for 12h;Reflux; | To a solution of 3-hydroxyanthranilic acid (1.93 g, 12.6 mmol) in saturated HCl MeOH (40 mL) was added p-toluenesulfonic acid (p-TsOH) monohydrate (95 mg, 0.5 mmol). The reaction mixture was stirred at reflux temperature for 12 h. The solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt. The organic layer was washed with saturated KHCO3 solution, water and brine, and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O. The insoluble material was filtered off. The filtrate was concentrated in vacuo. To a solution of methyl 3-hydroxyanthranilate (1.22 g, 7.37 mmol) in CH2Cl2 (10 mL) was added Et3N (1.85 g, 18.25 mmol), followed by dropwise addition of a solution of thiophosgene (923 mg, 8.03 mmol) in CH2Cl2 (2 mL) with stirring at ambient temperature for 5 min. The reaction mixture was concentrated in vacuo. The residue was dissolved in AcOEt. The organic layer was washed with 1-N HCl, water and brine and dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure to give a solid, which was crystallized from AcOEt/n-hexane to afford methyl 2-mercaptobenzo[d]oxazole-4-carboxylate (7a) (1.28 g, 84%). 2-bromo-N-(2,6-diisopropylphenyl)hexanamide (2e) was obtained from1 using 6-bromohexanoic acid in place of bromoacetic acid in a manner similar to that described for compound 3a. To a stirred solution of the thus obtained thiol (1.05 g, 5.0 mmol) and 2e (1.77 g, 5.0 mmol) in DMF (20 mL) were added K2CO3 (1.04 g, 7.5 mmol) and 18-crown-6 (132 mg, 0.5 mmol). The reaction mixture was stirred at 80 C for 2 h and diluted with water. The organic layer was extracted with Et2O, washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography and eluted with acetone/n-hexane (1:5) to give a solid, which was recrystallized from acetone/n-hexane to afford 12a (1.84 g, 76%) as colorless needles. | |
0.52 g | With thionyl chloride; for 16h;Reflux; | 3-Hydroxyanthranilic acid (0.47 g) was mixed with methanol (5.1 mL) and SOCl2 (0.11 mL) and reacted under reflux for 16 hours to obtain 3-hydroxyanthranilic acid methyl ester (3- hydroxyanthranilic acid methyl ester (yield: 0.52 g), which was dissolved in 3N NaOH (15 mL) with di-tert-butyl dicarbonate (0.89 mL)To obtain methyl 2- (tert-butoxycarbonylamino) -3-hydroxybenzoate [2- (tert-butoxycarbonylamino) -3-hydroxybenzoate, 0.58 g, compound 2].The anhydrous acetone solution (5.4 mL) of Compound 2 (0.29 g) was reacted with K2CO3 (0.5 g) and N- (3-bromopropyl) phthalimide, Synthesis of 2- (tert-butoxycarbonylamino) -3- [3- (1,3-dioxoisoindolin-2-yl) propoxy] benzoate - (1,3-dioxoisoindolin-2-yl) propoxy] bozoate, 0.32 g, compound 3} and compound 3 reacted with c-HCl (1.2 mL) with stirring at 100 for 48 hours and then concentrated under reduced pressure . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; hexane; toluene; for 16h; | A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3 -hydroxy anthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC (heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR = 0.70 min; [M+H]+ = 168.0. | |
In methanol; hexane; toluene; for 16h; | A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3 -hydroxy anthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by FC (heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR = 0.70 min; [M+H]+ = 168.0. | |
In methanol; hexane; toluene; | A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3-hydroxyanthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16 h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC (heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR=0.70 min; [M+H]+=168.0. |
In methanol; hexane; toluene; | A.2 Synthesis of benzo [ 1 ,4] oxazine-carboxylic acid derivatives; A.2.1 Synthesis of 2-amino-3-hydroxy-benzoic acid methyl ester; A solution of (trimethylsilyl)diazomethane in hexane (2.0 M, 10.9 mmol) is added dropwise (10 min) to a mixture of 3 -hydroxy anthranilic acid (9.93 mmol) in MeOH (10.5 mL) and toluene (42 mL). The mixture is stirred for 16h, concentrated in vacuo, diluted with ether and EtOAc and washed several times with water. The organic layer is dried over MgSO4 and concentrated under reduced pressure. The residue is purified by flash chromatography (gradient: heptane to heptane/EtOAc 7/3) to give the desired ester as a brown solid. LC-MS: tR = 0.70 min; [M+H]+ = 168.0. |