7-HYDROXYCOUMARIN-4-ACETIC ACID
- Product Name
- 7-HYDROXYCOUMARIN-4-ACETIC ACID
- CAS No.
- 6950-82-9
- Chemical Name
- 7-HYDROXYCOUMARIN-4-ACETIC ACID
- Synonyms
- NSC 65625;NSC 642907;UMBELLIFERONE-4-ACETIC ACID;B-UMBELLIFERONE ACETIC ACID;4-(CARBOXYMETHYL)UMBELLIFERONE;7-HYDROXYCOUMARIN-4-ACETIC ACID;7-HYDROXYCOUMARINYL-4-ACETIC ACID;7-HYDROXY-4-COUMARINYLACETIC ACID;4- Acotic acid -7- hydroxy coumarin;7-HydroxycouMarinyl-4-acetic acid 97%
- CBNumber
- CB9213782
- Molecular Formula
- C11H8O5
- Formula Weight
- 220.18
- MOL File
- 6950-82-9.mol
7-HYDROXYCOUMARIN-4-ACETIC ACID Property
- Melting point:
- 212 °C (dec.) (lit.)
- Boiling point:
- 523.5±50.0 °C(Predicted)
- Density
- 1.511±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMF: soluble
- form
- Crystalline Powder
- pka
- 4.24±0.10(Predicted)
- color
- Off-white to pale yellow
- λmax
- 326nm(MeOH)(lit.)
- BRN
- 204777
- InChI
- InChI=1S/C11H8O5/c12-7-1-2-8-6(3-10(13)14)4-11(15)16-9(8)5-7/h1-2,4-5,12H,3H2,(H,13,14)
- InChIKey
- BNHPMQBVNXMPDU-UHFFFAOYSA-N
- SMILES
- C1(=O)OC2=CC(O)=CC=C2C(CC(O)=O)=C1
- CAS DataBase Reference
- 6950-82-9(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 335665
- Product name
- 7-Hydroxycoumarinyl-4-acetic acid
- Purity
- 97%
- Packaging
- 1g
- Price
- $67.6
- Updated
- 2025/07/31
- Product number
- 335665
- Product name
- 7-Hydroxycoumarinyl-4-acetic acid
- Purity
- 97%
- Packaging
- 5g
- Price
- $91.7
- Updated
- 2025/07/31
- Product number
- H1501
- Product name
- 7-Hydroxycoumarin-4-acetic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $48
- Updated
- 2021/12/16
- Product number
- H1501
- Product name
- 7-Hydroxycoumarin-4-acetic Acid
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $148
- Updated
- 2022/04/27
- Product number
- H825135
- Product name
- 7-Hydroxycoumarin-4-acetic Acid
- Packaging
- 10g
- Price
- $215
- Updated
- 2021/12/16
7-HYDROXYCOUMARIN-4-ACETIC ACID Chemical Properties,Usage,Production
Uses
Fluorogenic substrate
Uses
7-Hydroxycoumarinyl-4-acetic acid was used in the synthesis of novel and specific enzyme substrates for Maroteaux-Lamy (MPS VI) and Morquio A (MPS IVA) diseases. It was also employed as ionic liquid matrice for MALDI-TOF MS of proteins, peptides and carbohydrates.
Uses
7-Hydroxycoumarin-4-acetic acid is a fluorescence label but can also be used as pH-indicator.
Synthesis
77-92-9
108-46-3
6950-82-9
GENERAL METHODS: Coumarin-4-acetic acid is a known compound (Manware et al., 2008). The reaction conditions for this compound were modified and optimized (Method A) to synthesize the analogues 2a-2f. These analogues were also synthesized by microwave-assisted methods (Method B). Method A: A mixture of citric acid (0.02 mol) and concentrated sulfuric acid (0.03 mol) was stirred at room temperature for 30 min. The mixture was placed in a boiling water bath to remove carbon monoxide (note: this needs to be done in a fume hood). Once the release of CO gas slowed down, the flask was removed from the water bath and left to stand for 15 minutes or until no more CO bubbles were produced in the reaction mixture. The reaction mixture was cooled to 10 °C and (un)substituted phenol (0.02 mol), pre-cooled to 10 °C, was added dropwise. The reaction mixture was stirred at room temperature for 48 h and then decanted onto ice. The precipitate was filtered and dissolved in saturated sodium bicarbonate solution. The solution was acidified to give intermediates 2a-2f. Method B: A mixture of citric acid (0.02 mol), concentrated sulfuric acid (0.03 mol), and (un)substituted phenol (0.02 mol) was placed in a microwave reactor and heated at 10% power for 4 min. The reaction mixture was poured onto crushed ice and processed according to the subsequent steps of Method A to obtain the target product. Yield of 7-hydroxycoumarin-4-acetic acid (2a): 67% for Method A and 78% for Method B; melting point: 170°C; IR (FT-IR) νmax (cm?1): 3210 (Ar C-H), 2924 (Al C-H), 1710 (C=O), 1701 (lactone C=O), 1458 (C=C), 1130 (C-O) , 1290 (C-OH); 1H-NMR (DMSO-d6, 400 MHz): δ 11.08 (1H, s, COOH), 7.41-6.98 (2H, m, H-5 and H-6), 6.69-6.23 (2H, m, H-8 and H-3), 4.93 (1H, dd, OH), 3.02-2.89 (2H, m , CH2); 13C-NMR (DMSO-d6, 100 MHz): δ 171.5 (C=O), 160.2 (C-2), 112.5 (C-3), 152.4 (C-4), 150.5 (C-8a), 135.2 (C-6), 124.8 (C-5), 122.9 (C-7), 120.1 (C-4a ), 104.1 (C-8), 37.0 (-CH2). HRMS (+ESI) [M+H]+: 221.0445 (calculated value), 221.0464 (measured value).
References
[1] Medicinal Chemistry Research, 2018, vol. 27, # 1, p. 61 - 71
[2] Tetrahedron Letters, 2012, vol. 53, # 48, p. 6598 - 6601,4
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5732 - 5735
[4] Journal of the Chemical Society, 1950, p. 170,172
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 3987,3989
7-HYDROXYCOUMARIN-4-ACETIC ACID Preparation Products And Raw materials
Raw materials
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View Lastest Price from 7-HYDROXYCOUMARIN-4-ACETIC ACID manufacturers
- Product
- 7-HYDROXYCOUMARIN-4-ACETIC ACID 6950-82-9
- Price
- US $500.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2018-08-04