Basic information
- CAS
93-35-6- Standard SMILES
O=c1ccc2ccc(O)cc2o1- InChIKey
ORHBXUUXSCNDEV-UHFFFAOYSA-N- Molecular formula
- C9H6O3
- Average molar mass
- 162.14 g/mol
- Monoisotopic mass
- 162.03169405
Overview
Umbelliferone is a hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7. It has a role as a fluorescent probe, a plant metabolite and a food component.
Names & identifiers
- Preferred name
- Umbelliferone
- IUPAC
- 7-hydroxychromen-2-one
- English name
- 7-Hydroxycoumarin
- Molecular formula
- C9H6O3
- Molecular weight
- 162.14
Names & synonyms
Umbelliferone7-hydroxycoumarin93-35-67-Hydroxy-2H-chromen-2-oneSkimmetinHydranginSkimmetineHydrangineUmbelliferon2H-1-Benzopyran-2-one, 7-hydroxy-7-hydroxychromen-2-one60Z60NTL4G
Show more names
Z-LIGUSTILIDEDichrin A7-Hydroxy-2H-benzopyran-2-oneLIGUSTILIDE, Z-7 HC
DTXSID5052626NSC-19790CHEBI:27510RefChem:6336DTXCID9031199202-240-37-hydroxycoumarine7-Oxycoumarin
Database identifiers
- CAS
93-35-6- PubChem CID
- 5281426
- DTXSID
DTXSID5052626- ChEMBL
CHEMBL51628- ChEBI
CHEBI:27510- UNII
- 60Z60NTL4G
- EC Number
- 202-240-3
- Nikkaji
- J1.764.002J、J4.673F
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 222
Experimental & physicochemical properties
Chemical Classes
Dyes -> Coumarin Dyes
UV filter
SpringerMaterials PropertiesDiamagnetic susceptibility
Melting Point230 - 232 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
Solid; [Merck Index] White or pale yellow powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
127.4 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5052626]
125.74 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
130.56 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
153.5 Ų [M+Na]+
Physicochemical properties
- Melting point
- 230 °C · 230 °C (dec.)(lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.2% (2 of 166) of reports.
Warning
H315 (98.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 166 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2H-1-Benzopyran-2-one, 7-hydroxy-
2H-1-Benzopyran-2-one, 7-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses liver effects, effects on plasma proteins, hypoglycemia, and changes in clotting factors in 45-day intermittent intraperitoneal studies of rats; [RTECS] An irritant; [Alfa Aesar MSDS] See Coumarin.
Hazard Classes and CategoriesSkin Irrit. 2 (98.8%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- GN6820000
- hs_code
- 29322980
- Toxicity
- LD50 intravenous in mouse: 450mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
Chemistry & industry
Pharmacology
Metabolism/Metabolites7-Hydroxycoumarin is a known human metabolite of 7-methoxycoumarin, coumarin, and 7-ethoxycoumarin.
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Found in many plants; Used in sunscreens, as intracellular and pH sensitive fluorescent indicator, and blood-brain barrier probe; [Merck Index] Active metabolite of coumarin. [ChemIDplus]
Synthetic Polymer MALDI Matrix Compounds
Applications
UsesA metabolite of Coumarin. The aglucon of skimmin. Present in many plants
Usesantifungal, phytoalexin
Uses7-Hydroxycoumarin is used as an intracellular pH sensitive fluorescent indicator & bloodbrain barrier probe. It is used as a sunscreen agent, and an optical brightener for textiles. It has also been used as a gain medium for dye lasers.
UsesIn sunscreen lotions and creams; as intracellular and pH sensitive fluorescent indicator and blood-brain barrier probe.
General DescriptionUmbelliferone is a naturally occurring coumarin, present in a variety of medicinal plants from the Apiaceae (Umbelliferae) family and also in plants from other families such as mouse-ear hawkweed.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
52 records
Compound notes
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