Basic information
- CAS
504-15-4- Standard SMILES
Cc1cc(O)cc(O)c1- InChIKey
OIPPWFOQEKKFEE-UHFFFAOYSA-N- Molecular formula
- C7H8O2
- Average molar mass
- 124.14 g/mol
- Monoisotopic mass
- 124.0524295
Overview
Orcinol is a 5-alkylresorcinol in which the alkyl group is specified as methyl. It has a role as an Aspergillus metabolite. It is a 5-alkylresorcinol and a dihydroxytoluene.
Names & identifiers
- Preferred name
- Orcinol
- IUPAC
- 5-methylbenzene-1,3-diol
- English name
- Orcinol
- Molecular formula
- C7H8O2
- Molecular weight
- 124.14
Names & synonyms
Show more names
Database identifiers
- CAS
504-15-4- PubChem CID
- 10436
- DTXSID
DTXSID2060123- ChEMBL
CHEMBL110059- ChEBI
CHEBI:16536- UNII
- 534PMB3438
- EC Number
- 207-984-2
- Nikkaji
- J6.215D
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 82.9
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 106 · 106-112 °C(lit.)
- Boiling point
- 290 °C · 290 °C
- Density
- 1.29 · 1.2900
- refractive index
- 1.4922 · 1.4922 (estimate)
- Flash point
- 159 °C · 159 °C
- storage temp.
- 20 °C · Store at <= 20°C.
- solubility
- 80 g/l · 80g/l
- pka
- 9.56 · 9.56±0.10(Predicted)
- form
- Crystalline Powder or Crystals
- color
- Pink-gray to pink-brown
- Water Solubility
- 80 g/L · 80g/L
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,6864
- BRN
- 1071903 · 1071903
- Stability
- Hygroscopic
- InChI
- 1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
- InChIKey
- OIPPWFOQEKKFEE-UHFFFAOYSA-N
- SMILES
- Cc1cc(O)cc(O)c1
- LogP
- 1.221 · 1.221 (est)
- CAS DataBase Reference
- 504 · 504-15-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 534 PMB3438 · 534PMB3438
- NIST Chemistry Reference
- 3 · 3,5-Dihydroxytoluene(504-15-4)
- EPA Substance Registry System
- 1 · 1,3-Benzenediol, 5-methyl- (504-15-4)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38-41-37/38-20/21/22
- Safety Statements
- 22 · 22-26-36-37/39
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 2100000 · VH2100000
- TSCA
- TSCA listed
- PackingGroup
- III
- HS Code
- 29072900 · 29072900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1,3-Benzenediol, 5-methyl-
Orcinol: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes convulsions and coma in subcutaneous lethal-dose studies of guinea pigs and rats; [RTECS] A skin and strong eye irritant; Harmful by ingestion; Prolonged or repeated exposure may cause eye injury; [Sigma-Aldrich MSDS] See 2-Methyl-1,4-hydroquinone, 1,3-Benzenediol, 2-methyl-, Resorcinol, and Cresol, all isomers.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- VH2100000
- ridadr
- 2811
- hs_code
- 29072900
- Toxicity
- LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
- risk_code
- 22-36/37/38-41-37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-26-36-37/39
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Uses & manufacturing
Applications
UsesOrcinol can be used to synthesize:Orcinol-containing azacryptands for use in optical amplifiers and light-emitting devices.Ternary co-crystal with 4,4′-bipyridine.Low-density carbon aerogels in the presence of formaldehyde.PEG-orcinol coumarins with potent tyrosinase inhibitory activity.
Preparation methods
PreparationOrcinol has been isolated from numerous lichen fungi (Robiquet, 1829) and can be synthesized by decarboxylation of orsellinic acid in Umbilicaria papulosa and Gliocladium roseum (Pettersson, 1965; Mosbach and Ehrensvard, 1966).Orcinol was first prepared by dehydroacetic acid, a conversion that involved ring-opening of the pyrone to a triketone. This early experiment helped establish the rich condensation chemistry of polyketides. It can be obtained by fusing extract of aloes with potash, followed by acidification.US3865884A: Preparation of orcinol
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Orcinol is a 5-alkylresorcinol in which the alkyl group is specified as methyl. It has a role as an Aspergillus metabolite. It is a 5-alkylresorcinol and a dihydroxytoluene.
Related reactions
Compound notes
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