Basic information
- CAS
87-20-7- Standard SMILES
CC(C)CCOC(=O)c1ccccc1O- InChIKey
PMGCQNGBLMMXEW-UHFFFAOYSA-N- Molecular formula
- C12H16O3
- Average molar mass
- 208.25 g/mol
- Monoisotopic mass
- 208.10994437
Overview
Isoamyl salicylate is a member of phenols and a benzoate ester. It is functionally related to a salicylic acid.
Names & identifiers
- Preferred name
- Isoamyl salicylate
- IUPAC
- 3-methylbutyl 2-hydroxybenzoate
- English name
- Isoamyl o-hydroxybenzoate
- Molecular formula
- C12H16O3
- Molecular weight
- 208.25
Names & synonyms
Isoamyl salicylate87-20-73-Methylbutyl 2-hydroxybenzoateIsopentyl salicylate3-Methylbutyl salicylateBenzoic acid, 2-hydroxy-, 3-methylbutyl esterSalicylic acid, isopentyl esterFEMA No. 20842-Hydroxybenzoic acid, 3-methylbutyl esterM25E4ZMR0NDTXSID9041655NSC-7952
Show more names
FEMA 2084OrchideeSanfoinNSC7952NSC 7952Liu isoaMylAMYLSALICATE
RefChem:149007DTXCID7021655201-730-4Isopentyl 2-HydroxybenzoateIsoamyl o-hydroxybenzoateIsopentyl o-hydroxybenzoate34377-38-3Isopentyl-2-hydroxyphenyl methanoate
Database identifiers
- CAS
87-20-7- PubChem CID
- 6874
- DTXSID
DTXSID9041655- ChEMBL
CHEMBL2260718- ChEBI
CHEBI:173601
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 201
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Fragrances
Fragrance Ingredient (Isoamyl salicylate) -> IFRA transparency List
Fragrance
LogP4.370
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density1.046-1.055
Flavoring AgentsEU Flavoring substances
Solubility
0.145 mg/mL at 25 °C
insoluble in water; soluble in organic solvents, oils
miscible at room temperature (in ethanol)
Boiling Point
277.00 to 278.00 °C. @ 760.00 mm Hg
277 °C
Refractive Index1.504-1.509
Physical Description
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 0.1% (1 of 711) of reports.
Warning
H302 (26.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 711 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 2-hydroxy-, 3-methylbutyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzoic acid, 2-hydroxy-, 3-methylbutyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 2-hydroxy-, 3-methylbutyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Isopentyl salicylate (EC: 201-730-4)
Isopentyl salicylate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (26.2%)
Safety data
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- VO4375000
- ridadr
- UN 3082 9/PG 3
- hs_code
- 29182300
- risk_code
- 51/53
- Signal word
- Warning
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
U.S. Production2023: 181,086 lb
Consumer UsesFragrance
Industry UsesFragrance
Household ProductsInformation on 23 consumer products that contain Isoamyl Salicylate in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Benzoic acid, 2-hydroxy-, 3-methylbutyl ester: ACTIVE
Applications
DescriptionIsoamyl salicylate has a characteristic aromatic, strong herbaceous, persistent odor and a bittersweet taste reminiscent of strawberry. May be prepared by esterification of salicylic acid with the isomeric amyl alcohols obtained from fusel oil and other sources.
OccurrenceReported found in Burley tobacco, grapes, black tea and rum
UsesIsoamyl Salicylate is used in preparation of Hydrogen Peroxide responsive Oxalic Acid derivatives for imaging and therapy.
Isoamyl o-hydroxybenzoate is used in perfumery and soaps. Extensively used in floral and non-floral perfume types: Very often in Carnation, Hyacinth, Orchid, Tretle, and almost inevitably in Fougere types. Its low cost and worldwide availability makes it one of the most important perfume chemicals. Occasionally used in "Root Beer" type flavors and certain Fruit flavors. Concentra- tion is usually mere traces (a few ppm in finished consumer product).
Related reactions
2 records
Compound notes
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