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4-isopropyl phenol
4-isopropyl phenol is a phenolic compound with woody, warm, spicy odor and burnt phenolic flavor used as a flavor and fragrance agent primarily sourced from cumin seed and eucalyptus.
General Material Description
4-isopropyl phenol, also known by trivial names such as 4-isopropylphenol and australol, is a phenolic compound chemically designated as phenol, 4-(1-methylethyl)- with a molecular formula of C9H12O. This compound is characterized by its woody, warm, and spicy odor, alongside a burnt phenolic flavor profile. It has multiple synonyms including p-cumenol and 4-hydroxycumene, reflecting its structural diversity in nomenclature. The compound occurs naturally in various botanical sources, notably cumin seed and eucalyptus polybractea, and is primarily used as a flavoring agent in spice formulations as well as a perfuming agent in fragrances. More information on its chemical properties and synonyms is available in the PubChem database. 4-isopropyl phenol is commercially extracted from natural materials such as cumin seed oil or produced synthetically for use in fragrance and flavor industries.
Occurrence, Applicability & Potential Uses
4-isopropyl phenol is found in nature primarily in cumin seed, where its concentration can reach up to 1900 mg/kg, and in cumin seed oil. It also occurs in eucalyptus polybractea and fried potato aromas, contributing characteristic woody and burnt phenolic notes. Its application includes use as a flavoring agent specifically for spice flavor profiles, supported by standards such as FEMA (US) which govern flavoring substances. Additionally, it is utilized as a perfuming agent in the fragrance industry due to its warm and woody sensory characteristics. Regulatory frameworks such as IFRA (Global) provide guidelines for its safe use in perfumery. The compound's sensory traits enable its incorporation in diverse products, ranging from food flavorings to cosmetic fragrances.
Physico-Chemical Properties Summary
4-isopropyl phenol exhibits a molecular weight of approximately 136.19 g/mol with a phenolic structure substituted by an isopropyl group at the para position. It melts at 60 to 64 °C and boils between 222 to 223 °C at standard atmospheric pressure, with a lower boiling range at reduced pressure (112 to 115 °C at 12 mm Hg). The compound has a moderate log P value of 2.9, indicating balanced lipophilicity, and a low vapor pressure of 0.147 mmHg at 25 °C, reflecting limited volatility under ambient conditions. It is soluble in alcohols and shows limited solubility in water at approximately 1102 mg/L at 25 °C. The flash point is around 95 °C (203 °F), which should be considered in formulation and handling. These properties influence its behavior in flavor and fragrance formulations, affecting evaporation rate, stability, and blending capability.
FAQ
What is 4-isopropyl phenol and what are its main characteristics?
4-isopropyl phenol is a phenolic aromatic compound featuring an isopropyl substitution at the para position of phenol. It possesses a woody, warm, and spicy odor with a burnt phenolic flavor profile. Known under various names like australol and p-cumenol, the compound naturally occurs in sources such as cumin seed and eucalyptus polybractea, thereby contributing to their characteristic aromas. It is primarily utilized in flavor and fragrance applications due to its sensory properties.
Where does 4-isopropyl phenol occur naturally, and how is it applied in industries?
This compound is naturally present in cumin seeds, cumin seed oil, and eucalyptus polybractea, as well as in fried potato aromas. It is valued for its woody and burnt phenolic notes, making it a choice ingredient in spice flavors and perfuming agents. In the flavor industry, it enhances spicy profiles, while in fragrance formulations it contributes warm, medicinal nuances. Usage levels and safety are regulated by standards such as FEMA (US) for flavorings and IFRA (Global) for fragrances.
What safety regulations and sourcing details apply to 4-isopropyl phenol?
4-isopropyl phenol is subject to stringent safety assessments in flavor and fragrance applications, with regulatory oversight from authorities such as the European Food Safety Authority (EFSA) and FEMA (US). Safety data indicate it may be harmful if swallowed and cause skin or eye irritation; thus, handling precautions are recommended. It is often sourced from natural extracts like cumin seed oil or synthesized for industrial use. Compliance with IFRA (Global) code of practice ensures safe concentration limits in fragrances, while flavor usage is monitored according to established maximum intake levels.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 4-propan-2-ylphenol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 99-89-8 |
| Pubchem (cid): | 7465 |
| Pubchem (sid): | 134972064 |
| Pherobase: | View |
| Publications by US Patents | |
| 3,946,080 - Flavouring and perfuming ingredients | |
| Furfurylthioacetone | |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Indirect Additives used in Food Contact Substances: | View |
| CHEMBL: | View |
| UM BBD: | Search |
| HMDB (The Human Metabolome Database): | HMDB29667 |
| FooDB: | FDB005302 |
| Export Tariff Code: | 2907.19.8000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 4-isopropyl phenol |
| Trivial Name | 4-Isopropylphenol |
| Short Description | phenol, 4-(1-methylethyl)- |
| Formula | C9 H12 O |
| CAS Number | 99-89-8 |
| Flavis Number | 4.073 |
| ECHA Number | 202-798-8 |
| FDA UNII | 9F59JOO816 |
| Nikkaji Number | J43.396I |
| Beilstein Number | 1363564 |
| MDL | MFCD00002372 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| Penta International | Santa Cruz Biotechnology |
| Sigma-Aldrich: Aldrich | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 136.19383239746 |
| Melting Point | 60 to 64°C @ 760 mm Hg |
| Boiling Point | 222 to 223°C @ 760 mm Hg |
| Boiling Point | 112 to 115°C @ 12 mm Hg |
| Vapor Pressure | 0.147 mmHg @ 25 °C |
| Flash Point TCC Value | 95.3 °C TCC |
| logP (o/w) | 2.9 |
| Solubility | |
| alcohol | Yes |
| water, 1102 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Woody | |
| woody, warm, spicy, medicinal | |
| General comment | At 1.00 % in dipropylene glycol. woody warm spicy medicinal |
| Flavor Type: Burnt | |
| burnt, phenolic | |
| General comment | Burnt phenolic |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Spice |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| C N - Corrosive, Dangerous for the environment. | |
| R 22 - Harmful if swallowed. R 34 - Causes burns. R 36/37/38 - Irritating to eyes, respiratory system, and skin. R 43 - May cause sensitisation by skin contact. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 23 - Do not breath vapour. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 28 - After contact with skin, wash immediately with plenty of water. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intravenous-mouse LD50 40 mg/kg BEHAVIORAL: SLEEP Journal of Medicinal Chemistry. Vol. 23, Pg. 1350, 1980. oral-mouse LD50 875 mg/kg Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 46(1), Pg. 94, 1981. intraperitoneal-mouse LDLo 250 mg/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 5, Pg. 339, 1953. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.24 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 420 (μg/person/day) | ||
| Threshold of Concern: | 1800 (μg/person/day) | ||
| Structure Class: | I | ||
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 0.50000 | 2.50000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.20000 | 1.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.50000 | 2.50000 | |
| Processed fruit (04.1): | 0.40000 | 2.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 1.00000 | 5.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.20000 | 1.00000 | |
| Bakery wares (07.0): | 2.00000 | 10.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.20000 | 1.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.20000 | 1.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.30000 | 1.50000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.50000 | 2.50000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.20000 | 1.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 | |
| Ready-to-eat savouries (15.0): | 2.00000 | 10.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.40000 | 2.00000 | |
Safety references
| European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies... |
| European Food Safety Authority (EFSA) reference(s): |
| Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring-substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 58 (FGE.58) Consideration of phenol derivatives evaluated by JECFA (55th meeting) structurally related to ring substituted phenolic substances evaluated by EFSA in FGE.22 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring-substituted phenolic substances from chemical groups 21 and 25 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):99-89-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7465 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2430 |
| WGK Germany:2 |
| 4-propan-2-ylphenol |
| Chemidplus:0000099898 |
| RTECS:SL5950000 for cas# 99-89-8 |