Cinnamyl alcohol

Base Information

• Chemical Name: Cinnamyl alcohol
• CAS No.: 104-54-1
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 29062990
• European Community (EC) Number: 203-212-3
• NSC Number: 623440,8775
• UNII: SS8YOP444F
• DSSTox Substance ID: DTXSID301314144
• Nikkaji Number: J9.304A,J106.769I
• Wikipedia: Cinnamyl alcohol,Cinnamyl_alcohol
• Wikidata: Q204030
• RXCUI: 1362889
• Metabolomics Workbench ID: 130876
• ChEMBL ID: CHEMBL324794
• Mol file: 104-54-1.mol

Synonyms:3-phenyl-2-propene-1-ol;3-phenylprop-2-en-1-ol;cinnamic alcohol;cinnamyl alcohol;cinnamyl alcohol, (E)-isomer;cinnamyl alcohol, titanium (4+) salt

Chemical Property of Cinnamyl alcohol

Chemical Property:

• Appearance/Colour: colourless solid
• Vapor Pressure: <0.01 mm Hg ( 25 °C)
• Melting Point: 30-33 °C(lit.)
• Refractive Index: 1.5819
• Boiling Point: 249.999 °C at 760 mmHg
• PKA: 0.852[at 20 ℃]
• Flash Point: 124.762 °C
• PSA: 20.23000
• Density: 1.044 g/cm³
• LogP: 1.69210
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble
• Water Solubility.: 1.8 g/L (20 ºC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Cinnamyl Alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38-43-36
• Safety Statements: 26-36/37-37/39-24-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)C=CCO
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/CO
• Description: As an organic compound, Cinnamyl alcohol has a very distinct sweet, spicy, hyacinth odour that is found in resins, balsams and cinnamon leaves. It is used commonly in the fragrance industry due to its distinctive odour, which can be applied as a deodorant, fragrance and additive in cosmetic products and in the formulation of bath products, body and hand products, such as soaps, toothpaste, deodorants, etc. Besides, it also finds application as a food additive in chewing gum, bakery products, candy and soft drinks. Naturally, Cinnamyl alcohol is occurrent only in small amount, thus its industrial demand is usually fulfilled by chemical synthesis starting from the reduction of cinnamaldehyde. Cinnamyl alcohol has been found to have a sensitising effect on some particular people, thus it is also considered as a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is caused by the Increased Histamine Release and cell-mediated Immunity. Occupational cases of contact dermatitis were reported in the perfurne industry. Patch tests can also be positive in food handlers. Cinnamic alcohol is contained in the "fragrance mix".
• Uses: Cinnamyl alcohol is valuable in perfumery for its odor and fixative properties. It is a component of many flower compositions (lilac, hyacinth, and lily of the valley) and is a starting material for cinnamyl esters, several of which are valuable fragrance materials. In flavor compositions, the alcohol is used for cinnamon notes and for rounding off fruit aromas. Cinnamic alcohol is a component in perfumed cosmetic products and deodorants; some perfumery uses (cinnamon; daffodil; hyacinth; jasmine); natural occurrence (cinnamon). Cinnamyl alcohol was used to study the alkylation of 2,4-di-tert-butylphenol by cinnamyl alcohol using aluminum-containing mesoporous ethane-silica catalyst. It was used to study gold nanoparticles supported on titanium dioxide catalysed oxidative coupling of alcohols and amines to form the corresponding imines. cinnamyl alcohol is naturally occurring in cinnamon bark, it can also be synthetically manufactured. It is used in cosmetics as a fragrance or flavoring agent.In perfumery; as deodorant in 12.5% solution in glycerol.

Technology Process of Cinnamyl alcohol

There total 196 articles about Cinnamyl alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

allylbenzene (300-57-2,57807-91-7) → 1-phenylpropene (637-50-3) + 3-Phenylpropenol (104-54-1) + 3-phenyl-propenal (104-55-2) + 1-phenyl-propan-1-one (93-55-0) + 1-phenyl-acetone (103-79-7,136675-26-8)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); 9-(2-mesityl)-10-methylacridinium perchlorate; In acetonitrile; at 20 ℃; for 16h; Reagent/catalyst;

DOI:10.1002/adsc.202100351

Reference yield: 62.0%

3-phenyl-propenal (104-55-2) → 3-Phenylpropenol (104-54-1) + 1,6-diphenyl-hexa-1,5-diene-3,4-diol (4403-20-7)

Guidance literature:

With LiPhInH₃; In diethyl ether; for 24h; Ambient temperature;

DOI:10.1016/0040-4039(95)00504-6

Reference yield: 40.3%

Cinnamic acid (621-82-9) → 3-Phenyl-1-propanol (122-97-4) + 3-Phenylpropenol (104-54-1) + 3-Phenylpropionic acid (501-52-0)

Guidance literature:

With hydrogen; In aq. phosphate buffer; at 40 ℃; for 24h; under 3750.38 Torr; pH=6.5; Reagent/catalyst; pH-value; chemoselective reaction; Autoclave;

DOI:10.1016/j.molcatb.2013.09.006

upstream raw materials:

benzyl bromide

lithium phenylacetylide

(E)-3-phenylpropenal

ethylmagnesium iodide

Downstream raw materials:

cinnamyl-furfuryl ether

triethyl[(3-phenyl-2-propenyl)oxy]silane

3-phenylpropanol triethylsilyl ether

3-Cinnamyloxy-butyronitril

Refernces

• 1、 Bandgar,Kasture. "Chemoselective protection of hydroxyl groups and deprotection of silyl ethers". . p. 1101 - 1104. Retrieved 2001.
• 2、 Szymczyk, Monika. "Unexpected course of Wittig reaction when using cinnamyl aldehyde as a substrate". . p. 264 - 266. Retrieved 2017.
• 3、 Kazemi,Kiasat. "Reduction of carbonyl compounds to the corresponding alcohols with isopropanol on dehydrated alumina under microwave irradiation". . p. 2255 - 2260. Retrieved 2002.
• 4、 Ni, Yan,Hagedoorn, Peter-Leon,Xu, Jian-He,Arends, Isabel W.C.E.,Hollmann, Frank. "Pyrococcus furiosus-mediated reduction of conjugated carboxylic acids: Towards using syngas as reductant". . p. 52 - 55. Retrieved 2014.
• 5、 Fleet, G.W.J.,Harding, P.J.C.. "SELECTIVITY IN THE ACID CATALYSED REDUCTION OF CARBONYL COMPOUNDS TO ALCOHOLS BY BIS(TRIPHENYLPHOSPHINE)COPPER(I) TETRAHYDROBORATE: REDUCTION OF ALDEHYDES IN THE PRESENCE OF KETONES". . p. 675 - 678. Retrieved 1981.
• 6、 Ma, Mingwei,Liu, Hui,Cao, Jingjie,Hou, Pan,Huang, Jiahui,Xu, Xingliang,Yue, Huijuan,Tian, Ge,Feng, Shouhua. "A highly efficient Cu/AlOOH catalyst obtained by in situ reduction: Catalytic transfer hydrogenation of ML into Γ-GVL". . p. 52 - 60. Retrieved 2019.
• 7、 Mirtaghizadeh, Mina,Setamdideh, Davood. "Ultrasonic-promoted selective reduction of aldehydes vs. ketones by NaBH4/PhCO2Na/H2O". . p. 1539 - 1543. Retrieved 2016.
• 8、 Araki, Shuki,Shimizu, Toshio,Johar, Perminder S.,Jin, Shun-Ji,Butsugan, Yasuo. "Preparation and Some Reactions of Allylic Indium Reagents". . p. 2538 - 2542. Retrieved 1991.
• 9、 Bernando, Joana R.,Florindo, Pedro R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.. "Reduction of aldehydes catalyzed by oxo-rhenium(V) complexes containing heterocyclic ligands". . p. 414 - 418. Retrieved 2015.
• 10、 Matsuoka, Hiroaki,Kondo, Kazuhiro. "Metal-free catalytic reduction of aldehydes, ketones, aldimines, and ketimines". . p. 1314 - 1317. Retrieved 2010.