Cinnamyl Alcohol

Product Name:

Cinnamyl alcohol

Synonyms:

(E)-3-phenyl-2-propen-1-ol;(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

CAS:

104-54-1

MF:

C9H10O

MW:

134.18

EINECS:

203-212-3

Product Categories:

chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Cosmetics;Pharmaceutical Intermediates;Benzhydrols, Benzyl & Special Alcohols

Mol File:

104-54-1.mol

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 | CINNAMYL ALCOHOL

refractive index 

1.5819

Fp 

>230 °F

storage temp. 

2-8°C

solubility 

H2O: soluble

form 

Fused Low Melting Crystalline Solid

Specific Gravity

1.044

color 

White

Water Solubility 

1.8 g/L (20 ºC)

JECFA Number

647

Merck 

14,2302

BRN 

1903999

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

OOCCDEMITAIZTP-QPJJXVBHSA-N

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

3-Phenyl-2-propen-1-ol (104-54-1)

Hazard Codes 

Xn

Risk Statements 

22-36/38-43-36

Safety Statements 

26-36/37-37/39-24-24/25

RIDADR 

2811

WGK Germany 

2

RTECS 

GE2200000

F 

10-23

TSCA 

Yes

HS Code 

29062990

Hazardous Substances Data

104-54-1(Hazardous Substances Data)

Toxicity

LD50 (g/kg): 2.0 orally in rats; >5.0 dermally in rabbits (Letizia)

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.

Chemical Properties

Cinnamyl alcohol has a pleasant, floral odor and bitter taste.

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.In perfumery; as deodorant in 12.5% solution in glycerol.

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.

Chemical 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.]