Esculetin
- Iupac Name：6,7-dihydroxychromen-2-one
- CAS No.: 305-01-1
- Molecular Weight：178.14154
- Modify Date.: 2022-11-29 10:51
- Introduction:
Esculetin is an active ingredient extracted mainly from the bark of Fraxinus rhynchophylla. Esculetin inhibits platelet-derived growth factor (PDGF)-induced airway smooth muscle cells (ASMCs) phenotype switching through inhibition of PI3K/Akt pathway. Esculetin has antioxidant, antiinflammatory, and antitumor activities[1].
Solid
Esculetin is a hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light. It has a role as an antioxidant, an ultraviolet filter and a plant metabolite.
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1. Names and Identifiers
- 1.1 Name
- Esculetin
- 1.2 Synonyms
2H-1-Benzopyran-2-one, 6,7-dihydroxy- 6,7-dihydroxy-2H-1-benzopyran-2-one 6,7-Dihydroxy-2H-chromen-2-one 6,7-DIHYDROXY-CHROMEN-2-ONE 6,7-Dihydroxycoumarin AESCULETIN AKOS 215-98 Asculetine CICHERINGENIN CICHORIGENIN Coumarin, 6,7-dihydroxy- Cryptotanshinone EINECS 206-161-5 Esculatin ESCULETOL Esculin aglycon LABOTEST-BB LT00233229 MFCD00006874
- 1.3 CAS No.
- 305-01-1
- 1.4 CID
- 5281416
- 1.5 EINECS(EC#)
- 206-161-5
- 1.6 Molecular Formula
- C9H6O4 (isomer)
- 1.7 Inchi
- InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
- 1.8 InChkey
- ILEDWLMCKZNDJK-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC(=O)OC2=CC(=C(C=C21)O)O
- 1.10 Isomers Smiles
- C1=CC(=O)OC2=CC(=C(C=C21)O)O
2. Properties
- 2.1 Density
- 1.563
- 2.1 Melting point
- 271-273℃
- 2.1 Boiling point
- 469.7 °C at 760 mmHg
- 2.1 Refractive index
- 1.594
- 2.1 Flash Point
- 201.4 °C
- 2.1 Precise Quality
- 178.02700
- 2.1 PSA
- 70.67000
- 2.1 logP
- 1.20420
- 2.1 Solubility
- Solubility Almost insoluble in boiling water, ether; soluble in hot ethanol, glacial acetic acid
- 2.2 Λmax
- 344(MeOH)nm
- 2.3 Appearance
- Light yellow powder
- 2.4 Storage
- 2-8°C
- 2.5 Chemical Properties
- YELLOWISH CRYSTALLINE POWDER
- 2.6 Color/Form
- Yellow powder
- 2.7 pKa
- 1.71(at 25℃)
- 2.8 Water Solubility
- Solubility Almost insoluble in boiling water, ether; soluble in hot ethanol, glacial acetic acid
- 2.9 Stability
- Stable under normal temperatures and pressures.
- 2.10 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.
- 3.2 Purification Methods
- It forms prisms from AcOH, aqueous EtOH or aqueous MeOH, and provides leaflets on sublimation in a vacuum. [Kagan J Am Chem Soc 88 2617 1966, Marby et al. Phytochemistry 4 492 1965.] Esculin (the 6-glucoside) has m 215o(dec), [] D -41o (c 5, pyridine). [Beilstein 18 III/IV 1322, 18/3 V 202.] Esculetin Preparation Products And Raw materials Preparation Products
- 3.3 Usage
- antifungal, hepatoprotective, IL-1 inhibitor
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S26;S37/39
- 4.1 Packing Group
- I; II; III
- 4.1 Hazard Declaration
- H315-H319-H335
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P261-P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- GN6382500
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
305-01-1Total: 2 Synthesis Route
8. Other Information
- 8.0 Merck
- 14,3697
- 8.1 BRN
- 152788
- 8.2 Target
- Value
- 8.3 Chemical Properties
- YELLOWISH CRYSTALLINE POWDER
- 8.4 Uses
- antifungal, hepatoprotective, IL-1 inhibitor
- 8.5 Uses
- In filters for absorption of ultraviolet light.
- 8.6 Definition
- ChEBI: A hydroxycoumarin that is umbelliferone in which the hydrogen at position 6 is substituted by a hydroxy group. It is used in filters for absorption of ultraviolet light.
- 8.7 General Description
-
Esculetin is a derivative of coumarin, found in various plant species including Cichorium intybus (chicory), Bougainvillea spectabilis, Artemisia capillaris, etc and leaves of Citrus limonia (Rutaceae), Ceratostigma willmottianum, etc. It exhibits multiple pharmacological activities and is found to be a potent inhibitor of cyclooxygenase, 5-lipoxygenase, 12-lipoxygenase, catechol-O-methyl transferase, NADPH oxidase and xanthine oxidase enzymes.
- 8.8 Usage
- In the presence of esculetin and HA14-1 (sc-205911) expression of the death receptor 4 (DR4) has been observed to be upregulated and extracellular-regulated kinase (ERK) to be activated. Other studies suggest that esculetin upregulates death receptor 5 (DR5) protein expression, and enhances TRAIL-induced apoptosis. It also inhibits the activity of 12-LO (12-lipoxygenase), and decreases leukotriene biosynthesis during 5-LO inhibition.
- 8.9 Collision Cross Section
- 129.5 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
- 8.10 Mesh
- Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
- 8.11 Mesh Entry Terms
- 6,7-dihydroxycoumarin
9. Computational chemical data
- Molecular Weight: 178.14154g/mol
- Molecular Formula: C9H6O4
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 178.02660867
- Monoisotopic Mass: 178.02660867
- Complexity: 248
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 66.8
- Heavy Atom Count: 13
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAACBAAAAGgAACAAADASAmAAwDoAABgCIAiDSCAACCAAgIAAIiAAGiMgNJyKGMRqCeiGlwBUJuYfA4DwOIQABCAAIQABCAAIQABCAAAAAAAAAAA==
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Esculetin
- Purity:99%Packing: 200kg/bag FOB
- Price: 3 USD/kilogram
- Time: 2023/04/23
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Esculetin
- Purity:99%Packing: 200kg/bag FOB
- Price: 0 USD/kilogram
- Time: 2023/05/22
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Esculetin
- Purity:99%Packing: 200kg/bag FOB
- Price: 1 USD/kilogram
- Time: 2023/05/26
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11. Realated Product Infomation
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