Umbelliferone
7-Hydroxycoumarin
CAS: 93-35-6
Molecular Formula: C9H6O3
Umbelliferone - Names and Identifiers
| Name | 7-Hydroxycoumarin |
| Synonyms | SKIMMETIN UMBELLIFERON UMBELLIFERONE Z-LIGUSTILIDE Umbelliferone 7-Hydroxycoumarin 7-HYDROXYCOUMARIN 7-hydroxy coumarin 7-hydroxy-2H-chromen-2-one 7-Hydroxy-2H-1-Benzopyran-2-One 7-Hydroxy-2H-1-benzopyran-2-one 2H-1-BENZOPYRAN-2-ONE, 7-HYDROXY- 3-BUTYLIDEN-4,5-DIHYDRO-3H-ISOBENZOFURAN-1-ONE |
| CAS | 93-35-6 |
| EINECS | 202-240-3 |
| InChI | InChI=1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H |
| InChIKey | ORHBXUUXSCNDEV-UHFFFAOYSA-N |
Umbelliferone - Physico-chemical Properties
| Molecular Formula | C9H6O3 |
| Molar Mass | 162.14 |
| Density | 1.2599 (rough estimate) |
| Melting Point | 230°C (dec.)(lit.) |
| Boling Point | 248.82°C (rough estimate) |
| Flash Point | 181.2°C |
| Water Solubility | 1 g/100 mL (100 ºC) |
| Solubility | Soluble in alcohol, chloroform and acetic acid, soluble in dilute lye, insoluble in ether, slightly soluble in boiling water (1g/100ml). |
| Vapor Presure | 2.2E-06mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | Off-white to beige-brownish |
| Maximum wavelength(λmax) | ['320nm'] |
| Merck | 14,9847 |
| BRN | 127683 |
| pKa | 7.11(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5380 (estimate) |
| MDL | MFCD00006878 |
| Physical and Chemical Properties | White needle crystal. Melting point 225-228 ℃(230-232 ℃). Soluble in alcohol, chloroform and acetic acid, soluble in dilute lye, insoluble in ether, slightly soluble in boiling water (1g/100ml). The solution shows blue fluorescence. Can sublimate. |
Umbelliferone - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | GN6820000 |
| HS Code | 29322980 |
| Toxicity | LD50 intravenous in mouse: 450mg/kg |
Umbelliferone - Reference
| Reference Show more | 1. Zhang Hongbing, Yang Chengzi. Quality investigation of radix et Rhizoma praeruptoris [J]. Fujian Traditional Chinese Medicine, 2013, 44(005):51-53. 2. Simultaneous determination of 12 kinds of methoxyflavonoids and coumarins in citrus juice by Li Guijie, Tan Xiang, Wang Hua, Wu Houyan, Russell ROUSEFF.HPLC-DAD-FLD [J]. Food Science, 2017, 38(20):112-118. 3. [IF = 4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum." Molecules. 2016 Apr;21(4):468 4. Manjie Gao et al. [IF = 9.811]. "High-crystality Covalent Organic Framework Synthesized in Deep eutictic Solvent: Potentially Effective Adsorbents Alternative to Macroporous Resin for Flavonoids."Chem Mater. 2021;33(20):8036-8051 5. [IF=9.229] Linlin Deng et al."Highly Crystalline Covalent Organic Frameworks Act as a Dual-Functional Fluorescent-Sensing Platform for Myricetin and Water, and Adsorbents for Myricetin."Acs Appl Mater Inter. 2021;13(28):33449-33463 6. [IF=5.753] Liu Man et al."Constructing a Core Collection of the Medicinal Plant Angelica biserrata Using Genetic and Metabolic Data."Front Plant Sci. 2020 Dec;0:2099 7. [IF=4.845] Liang Yang et al."Sustainable natural bioresources in crop protection: antimicrobial hydroxycoumarins induce membrane depolarization-associated changes in the transcriptome of Ralstonia solanacearum."Pest Manag Sci. 2021 Nov;77(11):5170-5185 8. [IF=4.268] Wei-Feng Wu et al."7-Hydroxycoumarin protects against cisplatin-induced acute kidney injury by inhibiting necroptosis and promoting Sox9-mediated tubular epithelial cell proliferation."Phytomedicine. 2020 Apr;69:153202 9. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 10. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 |
Umbelliferone - Reference Information
| pH range of acid-base indicator discoloration | Non/ uoresce (6.5) to blue / uoresce (8.0) |
| Main application | fluorecent brighteners, fungicides, cosmetics, detection of microorganizations, treatment of suppressed neurotransmission disorders, Alzheimer's disease, vascular and immunological edema cancer, early diagnosis of stroke, drug-coated coronary stent system |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | 7-hydroxycoumarin is white needle-like crystal, it can be used as fluorescent indicator and acid-base indicator (pH 6.5-8.0). |
| biological activity | Umbelliferone (7-hydroxy coumarin), a natural product of the coumarin family, is a fluorescent compound that can be used as a sunscreen. |
| Use | is used as fluorescent indicator and acid-base indicator (pH 6.5-8.0). for content determination/identification/pharmacological experiments. Pharmacological Efficacy: anticoagulant, antioxidant, anti-tumor, anti-virus, anti-HIV, cytotoxicity and other biological activities. |
| production method | condensation of 2, 4-dihydroxyacetophenone with malic acid in the presence of sulfuric acid at 90-130 °c, umbelliferone was obtained by eliminating the acetyl group. |
Last Update：2024-04-18 10:46:14
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