| Identification | More | [Name]
Cinnamyl alcohol | [CAS]
104-54-1 | [Synonyms]
3-HYDROXY-1-PHENYL-1-PROPENE
3-PHENYL-2-PROPEN-1-OL
3-PHENYL-2-PROPENE-1-OL
3-PHENYL-2-PROPEN-L-OL
3-PHENYLALLYL ALCOHOL
3-PHENYLALLYLOL
3-PHENYLPROPENOL
CINNAMIC ALCOHOL
CINNAMYL ALCOHOL
FEMA 2294
STYRYL CARBINOL
TRANS-3-PHENYL-2-PROPEN-1-OL
TRANS-CINNAMYL ALCOHOL
(2E)-3-Phenyl-2-propen-1-ol
1-Phenyl-1-propen-3-ol
2-Propen-1-ol,3-phenyl-
3-Fenyl-2-propen-1-ol
3-phenyl-2-propen-1-o
3-Phenyl-2-propenol
3-phenyl-prop-2-en-1-ol | [EINECS(EC#)]
203-212-3 | [Molecular Formula]
C9H10O | [MDL Number]
MFCD00002921 | [Molecular Weight]
134.18 | [MOL File]
104-54-1.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless solid | [Melting point ]
30-33 °C(lit.)
| [Boiling point ]
250 °C(lit.)
| [density ]
1.044 g/mL at 25 °C(lit.)
| [vapor density ]
4.6 (vs air)
| [vapor pressure ]
<0.01 mm Hg ( 25 °C)
| [FEMA ]
2294 | [refractive index ]
1.5819 | [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
H2O: soluble | [form ]
Fused Low Melting Crystalline Solid | [pka]
0.852[at 20 ℃] | [color ]
White | [Specific Gravity]
1.044 | [Odor]
at 100.00 %. sweet balsam hyacinth spicy green powdery cinnamic | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Odor Type]
balsamic | [Water Solubility ]
1.8 g/L (20 ºC) | [JECFA Number]
647 | [Merck ]
14,2302 | [BRN ]
1903999 | [Contact allergens]
Cinnamyl alcohol occurs (in esterified form) in storax,
Myroxylon pereirae, cinnamon leaves, and hyacinth
oil. It is obtained by the alkaline hydrolysis of storax
and prepared synthetically by reducing cinnamal diacetate
with iron filings and acetic acid, and from cinnamaldehyde
by Meerwein-Ponndorf reduction with
aluminum isopropoxide. Cinnamic alcohol is contained
in the “fragrance mix.” As a fragrance allergen,
it has to be mentioned by name in cosmetics within the
EU. Occupational cases of contact dermatitis were
reported in perfume industry. Patch tests can be positive
in food handlers. | [InChIKey]
OOCCDEMITAIZTP-QPJJXVBHSA-N | [LogP]
1.452 at 25℃ | [Uses]
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. | [CAS DataBase Reference]
104-54-1(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Propen-1-ol, 3-phenyl-(104-54-1) | [EPA Substance Registry System]
104-54-1(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
colourless solid | [Uses]
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. | [Definition]
ChEBI: A primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C2C bond unspecified). | [Uses]
In perfumery; as deodorant in 12.5% solution in glycerol. | [Occurrence]
Occurring as an ester or in the free state in hyacinth, Aristolochia clematis, Xanthorrhoea hastilis and in the
essence of daffodil flowers. It is also reported found in guava fruit and peel, lemon peel oil, cassia leaf, Bourbon vanilla and cinnamon
bark, leaf and root. | [Aroma threshold values]
Detection: 1 ppm; cis- form, 81 ppb; trans- form, 2.8 ppm | [Taste threshold values]
Taste characteristics at 20 ppm: green, floral, spicy and honey with a fermented yeasty nuance. | [Synthesis Reference(s)]
Chemistry Letters, 5, p. 581, 1976
The Journal of Organic Chemistry, 59, p. 6378, 1994 DOI: 10.1021/jo00100a046
Tetrahedron Letters, 34, p. 257, 1993 DOI: 10.1016/S0040-4039(00)60561-0 | [General Description]
This reference material (RM) is produced and certified in accordance with ISO/IEC 17025. This RM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com. | [Flammability and Explosibility]
Notclassified | [Synthesis]
Obtained originally by saponification of extraction from storax; synthetically, by reduction of cinnamaldehyde with
sodium or potassium hydroxide. | [Purification Methods]
Crystallise the alcohol from diethyl ether/pentane. [Beilstein 6 I 281.] |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin .
R43:May cause sensitization by skin contact.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S37/39:Wear suitable gloves and eye/face protection .
S24:Avoid contact with skin . | [RIDADR ]
2811 | [WGK Germany ]
2
| [RTECS ]
GE2200000
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
29062900 | [Hazardous Substances Data]
104-54-1(Hazardous Substances Data) | [Toxicity]
LD50 (g/kg): 2.0 orally in rats; >5.0 dermally in rabbits (Letizia) |
| Questions And Answer | Back Directory | [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.
| [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.
| [Preparation]
Cinnamyl alcohol is prepared on an industrial scale by reduction of cinnamaldehyde. Three methods are particularly useful:
1) In the Meerwein–Ponndorf reduction, cinnamaldehyde is reduced to cinnamic alcohol (yield about 85%) with isopropyl or benzyl alcohol in the presence of the corresponding aluminum alcoholate.
2) A 95% yield of Cinnamyl alcohol is obtained by selective hydrogenation of the carbonyl group in cinnamaldehydewith, for example, an osmium–carbon catalyst.
3) High yields of Cinnamyl alcohol can be obtained by reduction of cinnamaldehyde with alkali borohydrides. Formation of dihydrocinnamic alcohol is thus avoided.
| [References]
https://en.wikipedia.org/wiki/Cinnamyl_alcohol
http://www.huidziekten.nl/allergie/stoffen/cinnamic-alcohol.htm
https://www.ulprospector.com/en/na/Food/Detail/13286/411638/Cinnamic-Alcohol
http://www.cosmeticsinfo.org/ingredient/cinnamyl-alcohol-0
https://pubchem.ncbi.nlm.nih.gov/compound/cinnamyl_alcohol#section=Top
http://www.somaiya.com/products/chemicals-pipeline/cinnamic-alcohol-1 |
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