Cinnamaldehyde
- Iupac Name：(E)-3-phenylprop-2-enal
- CAS No.: 104-55-2
- Molecular Weight：132.16
- Modify Date.: 2022-11-05 16:23
- Introduction: Cinnamic aldehyde is used as a flavoring agent, ingredientof fragrance in soft drinks, ice creams, dentifrices,pastries, chewing-gum, etc. It can induce both contacturticaria and delayed-type reactions. It can be implicated in contact dermatitis in those who work in theperfume industry or food handlers. Cinnamic aldehydeis contained in the "fragrance mix".
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1. Names and Identifiers
- 1.1 Name
- Cinnamaldehyde
- 1.2 Synonyms
2-Propenal, 3-phenyl- 3-Phenyl-2-propen-1-al 3-Phenyl-2-propenal 3-Phenyl-2-propenaldehyde 3-Phenyl-2-propene-1-al 3-Phenylacrolein 3-Phenylacrylaldehyde 3-PHENYLPROPENAL Abion CA AKOS B004060 AKOS BBS-00003207 Benzylideneacetaldehyde Cassia aldehyde Cinnacure Cinnamal CINNAMALDEHYDE, TRANS- CINNAMIC ALDEHYDE Cinnamite Cinnamyl aldehyde FEMA 2286 LABOTEST-BB LT00939010 NSC 16935 NSC 40346 Phenylacrolein XC 800 Zimtaldehyde β-Phenylacrolein
- 1.3 CAS No.
- 104-55-2
- 1.4 CID
- 637511
- 1.5 EINECS(EC#)
- 203-213-9; 604-377-8
- 1.6 Molecular Formula
- C9H8O (isomer)
- 1.7 Inchi
- InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+
- 1.8 InChkey
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N
- 1.9 Canonical Smiles
- C1=CC=C(C=C1)C=CC=O
- 1.10 Isomers Smiles
- C1=CC=C(C=C1)/C=C/C=O
2. Properties
- 2.1 Density
- 1.05 g/mL at 25 °C(lit.)
- 2.1 Melting point
- ?9-?4 °C(lit.)
- 2.1 Boiling point
- 250-252 °C(lit.)
- 2.1 Refractive index
- n20/D 1.622(lit.)
- 2.1 Flash Point
- 160 °F
- 2.2 Precise Quality
- 132.05800
- 2.2 PSA
- 17.07000
- 2.2 logP
- 1.89870
- 2.2 Solubility
- 1g/l soluble
- 2.3 VaporDensity
- VAPOR DENSITY: 4.6 (AIR= 1)
- 2.4 Appearance
- yellow liquid with an odour of cinnamon
- 2.5 Atmospheric OH Rate Constant
- 4.80e-11 cm3/molecule*sec
- 2.6 Chemical Properties
- Cinnamaldehyde exists as yellowish to greenish-yellow oily liquid with a Strong pungent, spicy, cinnamon odor. It is normally insoluble in water and many organic solvents but is miscible with alcohol and other flavoring oils. Exposure to air will result in thickening and oxidation.
- 2.7 Color/Form
- Yellowish oily liquid
GREENISH-YELLOW LIQUID
- 2.8 Odor
- PUNGENT, SPICY NOTE
- 2.9 Odor Threshold
- 50-750 ppb
- 2.10 Water Solubility
- Slightly soluble
- 2.11 Spectral Properties
- MAX ABSORPTION (ALCOHOL): 291 NM (LOG E= 4.40)
SADTLER REF NUMBER: 1490 (IR, PRISM)
Index of refraction: 1.618-1.623 at 20 deg C/D
- 2.12 Stability
- Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
3. Use and Manufacturing
- 3.1 Agricultural Uses
- Fungicide, Insecticide: Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casingfor mushrooms, row crops, turf and all food commodities.Not listed for use in EU countries.
- 3.2 General Description
- Yellow oily liquid with a cinnamon odor and sweet taste.
- 3.3 Potential Exposure
- Botanical fungicide and insecticide. Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casing for mushrooms, row crops, turf, and all food commodities. Not listed for use in EU countries.
- 3.4 Shipping
- UN1989 Aldehydes, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid
- 3.5 Usage
- Cinnamaldehyde is used in flavor and perfumes.It occurs in cinnamon oils.
- 3.6 Waste Disposal
- Incineration. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Cinnamaldehyde Preparation Products And Raw materials Raw materials
4. Safety and Handling
- 4.1 Symbol
- GHS07;
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- 36/37/38-43
- 4.1 Safety Statements
- 26-36/37
- 4.1 Exposure Standards and Regulations
- Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Cinnamaldehyde is included on this list.
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Cinnamaldehyde is included on this list.
- 4.2 Packing Group
- I; II; III
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 1.90
- 4.3 Fire Hazard
- Cinnamaldehyde is combustible.
- 4.4 Other Preventative Measures
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
User should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Cinnacure A3005/
Agricultural use requirements. Use this product only in accordance with its labeling and with Worker Protection Standard, 40 CFR part 170. ... Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 4 hours. /Cinnacure A3005/
Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the nean high water mark. /Cinnacure A3005/
- 4.5 Hazard Declaration
- H315; H317; H319; H335
- 4.5 Cleanup Methods
- SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
Do not contaminate water by cleaning of equipment or disposal of wastes. /Cinnacure A3005/
- 4.6 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Do not use, pour, spill or store near heat or open flame. /Cinnacure A3005/
- 4.7 RIDADR
- UN8027
- 4.7 Fire Fighting Procedures
- CO2, dry chemical, or appropriate foam.
- 4.8 Safety Profile
- Poison by intravenous and parenteral routes. Moderately toxic by ingestion and intraperitoneal routes. A severe human skin irritant. Mutation data reported. Combustible liquid. May ipte after a delay period in contact with NaOH. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.
- 4.9 Formulations/Preparations
- Perfume grade, FCC, 98% min purity.
Chief ingredient (up to 90%) of oil of cinnamon.
Cinnacure A3005; Active ingredient 30.00% Cinnamaldehyde
Cinnacure Ready to Use; Active ingredient 0.255% Cinnamaldehyde
- 4.10 Incompatibilities
- Aldehydes are frequently involved in selfcondensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, ketones, azo dyes, caustics, boranes, hydrazines
- 4.11 WGK Germany
- 3
- 4.11 RTECS
- GD6476000
- 4.11 Protective Equipment and Clothing
- Agricultural use requirements. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, water, is: Coveralls, waterproof gloves, shoes plus socks./Cinnacure A3005/
Long-sleeved shirt and long pants, protective eyewear, shoes plus socks, waterproof gloves.
- 4.12 Reactivities and Incompatibilities
- Rags soaked in sodium hydroxide and in /cinnamaldehyde/ overheated and ignited owing to aerobic oxidation when they came into contact in a waste bin.
- 4.13 Skin, Eye, and Respiratory Irritations
- Primary eye irritant ... Dermal irritant.
No primary dermal irritation was observed in human subjects exposed for 48 hours to a solution of a 3% active ingredient, while severe primary dermal irritation was observed in human subjects after exposure to 8% active ingredient.
- 4.14 Toxicity
- LD50 in rats (mg/kg): 2220 orally (Jenner)
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Dermal, Category 4
Skin irritation, Category 2
Skin sensitization, Category 1
Eye irritation, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H312 Harmful in contact with skin H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation |
| Precautionary statement(s) | |
| Prevention | P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
104-55-2Total: 176 Synthesis Route
9. Computational chemical data
- Molecular Weight: 132.16g/mol
- Molecular Formula: C9H8O
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 132.057514874
- Monoisotopic Mass: 132.057514874
- Complexity: 121
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 17.1
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADACgmAIwAIAAAACIAihSgAACAAAgAAAIiAAAAMgIICKAERCAIAAggAAIiYcAgAAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
The molecule shown by the OP is cis (Z) cinnamic aldehyde - not the ordinary trans (E) cinnamaldehyde. Trans cinnamaldehyde melts at -7.5C, so is liquid at room temperature, and while the melting point of the cis wasn't available, it has been described as a yellowish liquid. The trans isomer is ava...
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When was the name cinnamaldehyde officially changed to trans -3-phenylprop-2-enal?
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I was given some data to determine what the unknown compound was and figured out that it was cinnamaldehyde . After reviewing the classification test given to me by my professor, I was a bit confused as to why it would pass the ferric chloride test as well as pass a Lucas test but yet show no react...
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I recently watched a video on extracting cinnamaldehyde from cinnamon using dichloromethane as a solvent. I would like to attempt the process. However, I would prefer not to use haloalkanes because of the health risks. Would ethyl acetate be a suitable replacement solvent for dichloromethane in ext...
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