Basic information
- Standard SMILES
CC(C)c1ccc(O)cc1- InChIKey
YQUQWHNMBPIWGK-UHFFFAOYSA-N- Molecular formula
- C9H12O
- Average molar mass
- 136.19 g/mol
- Monoisotopic mass
- 136.088815
Overview
4-isopropylphenol is a member of the class of phenols that is phenol which is carrying an isopropyl group at position 4. It has a role as a flavouring agent. It derives from a hydride of a cumene.
Names & identifiers
- Preferred name
- 4-Isopropylphenol
- IUPAC
- 4-propan-2-ylphenol
- English name
- 4-Isopropylphenol
- Molecular formula
- C9H12O
- Molecular weight
- 136.19
Names & synonyms
4-Isopropylphenol99-89-8P-ISOPROPYLPHENOLp-CumenolAustralol4-(Propan-2-Yl)PhenolPhenol, 4-(1-methylethyl)-1-Hydroxy-4-isopropylbenzene4-propan-2-ylphenolProdox 133para-isopropylphenolDTXSID5042299
Show more names
4-(1-methylethyl)-PhenolNSC 1888prodox1334-Isopropylphe4-HYDROXYCUMOLp-Hydroxycumene
9F59JOO816NSC-1888DTXCID3022299CHEBI:167172RefChem:524344202-798-84-(1-Methylethyl)phenol4-Hydroxycumene
Database identifiers
- CAS
99-89-8- PubChem CID
- 7465
- DTXSID
DTXSID5042299- ChEMBL
CHEMBL29966- ChEBI
CHEBI:167172- UNII
- 9F59JOO816
- EC Number
- 202-798-8
- Nikkaji
- J43.396I
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 90.9
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phenols
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (4-Isopropylphenol) -> IFRA transparency List
LogP2.90
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point222.00 to 223.00 °C. @ 760.00 mm Hg
Melting Point62.3 °C
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description
Light yellow crystalline solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section134.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5042299]
Physicochemical properties
- Melting point
- 59 · 59-61 °C (lit.)
- Boiling point
- 212 · 212-213 °C (lit.)
- Density
- 0.99 · 0.9900
- vapor density
- 1 · >1 (vs air)
- refractive index
- 1.5228 · 1.5228
- FLAVIS Number
- 4.073 · 04.073 | 4-Isopropylphenol
- Flash point
- 108 °C · 108°C
- storage temp.
- 2 °C · Store at +2°C to +8°C.
- solubility
- Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
- pka
- 10.19 · 10.19±0.13(Predicted)
- form
- Crystalline Mass or Crystals
- color
- White to beige-brown
- Odor
- 1 % · at 1.00 % in dipropylene glycol. woody warm spicy medicinal
- Odor Type
- woody
- Water Solubility
- Slightly soluble in water, soluble in ethanol and ethyl ether.
- BRN
- 1363564 · 1363564
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C9H12O/c1-7(2)8-3-5-9(10)6-4-8/h3-7,10H,1-2H3
- InChIKey
- YQUQWHNMBPIWGK-UHFFFAOYSA-N
- SMILES
- CC(C)c1ccc(O)cc1
- LogP
- 2.9 · 2.900
- CAS DataBase Reference
- 99 · 99-89-8(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- ISOPROPYLPHENOL, P-
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 F59JOO816 · 9F59JOO816
- NIST Chemistry Reference
- 4 · Phenol, 4-(1-methylethyl)-(99-89-8)
- EPA Substance Registry System
- p-Isopropylphenol (99-89-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H317-H412
- Precautionary statements
- 501 · P501-P273-P272-P260-P270-P264-P280-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 22 · 22-34-43-52/53
- Safety Statements
- 26 · 26-36/37/39-45-61
- RIDADR
- 2430 · UN 2430 8/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 5950000 · SL5950000
- Hazard Note
- Corrosive/Harmful
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29071900 · 29071900
- Storage Class
- 8 B · 8B - Non-combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1430 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: Phenol, 4-(1-methylethyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 14-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24873
Phenol, 4-(1-methylethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Propyl and butyl phenols
Hazards Summary
Causes altered sleep time (including change in righting reflex) and dyspnea in intraperitoneal lethal-dose studies of mice (LD50 = 250 mg/kg); [RTECS] Causes burns; Inhalation may cause sensitization and corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Sigma-Aldrich MSDS] See p-tert-Butylphenol.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Toxicity Summary
The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of 4-isopropylphenol as described in this fragrance ingredient safety assessment. The data for a read-across compound, p-cresol (CAS # 106-44-5), indicate that 4-isopropylphenol is not expected to be genotoxic. The calculated Margin of Exposure (MOE) for repeated dose and reproductive toxicity is greater than 100, based on data for p-cresol. Data for another read-across compound, thymol (CAS # 89-83-8), show no safety concerns for skin sensitization at current usage levels as a fragrance ingredient. An evaluation based on ultraviolet/visible (UV/Vis) spectra indicates that 4-isopropylphenol is not likely to cause photoirritation or photoallergenicity. The local respiratory toxicity was assessed using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposure to 4-isopropylphenol is below the TTC (1.4 mg/day).
Environmental Fate/Exposure Summary
The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of 4-isopropylphenol as described in this fragrance ingredient safety assessment. It was found not to be Persistent, Bioaccumulative, and Toxic (PBT) according to the International Fragrance Association (IFRA) Environmental Standards. Its risk quotients, calculated based on its current volume of use (VoU) in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are less than 1.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- SL5950000
- ridadr
- UN 2430 8/PG 3
- hs_code
- 29071900
- risk_code
- 22-34-43-52/53
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- hazard_note
- Corrosive/Harmful
- safety_code
- 26-36/37/39-45-61
- hazard_class
- 8
- Storage Class
- 8B - Non-combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H302-H314-H317-H412
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- Precautionary statements
- P501-P273-P272-P260-P270-P264-P280-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Chemistry & industry
Pharmacology
Metabolism/Metabolites4-Isopropylphenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-propan-2-ylphenoxy)oxane-2-carboxylic acid.
Cellular LocationsMembrane
Uses & manufacturing
Use ClassificationFragrance Ingredients
General Manufacturing InformationPhenol, 4-(1-methylethyl)-: ACTIVE
Applications
Uses4-Isopropylphenol was used in the synthesis of vinyl compounds. It is used as a flavor & fragrance agent in cosmetics.
Uses4-Isopropylphenol is an Impurity of Propofol (P829750).
General DescriptionSonochemical degradation of 4-Isopropylphenol has been studied.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: 4-isopropylphenol is a member of the class of phenols that is phenol which is carrying an isopropyl group at position 4. It has a role as a flavouring agent. It derives from a hydride of a cumene.
Related reactions
76 records
Linked notes
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