3-Phenyl-1-propanol CAS 122-97-4

Introduction：Basic information about 3-Phenyl-1-propanol CAS 122-97-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

3-Phenyl-1-propanol Basic information

• Product Name: 3-Phenyl-1-propanol
• Synonyms: (3-Hydroxypropyl)benzene;1-Hydroxy-3-phenylpropane;1-Propanol, 3-phenyl-;3- Phenylprophyl alcohol;3-Benzenepropanol;3-phenyl-1-propano;3-Phenyl-n-propanol;3-phenylpropan-
• CAS: 122-97-4
• MF: C9H12O
• MW: 136.19
• EINECS: 204-587-6
• Product Categories: 122-97-4;11
• Mol File: 122-97-4.mol

3-Phenyl-1-propanol Chemical Properties

• Melting point: −18 °C(lit.)
• Boiling point: 119-121 °C12 mm Hg(lit.)
• density: 1.001 g/mL at 20 °C(lit.)
• vapor pressure: 1.13-25Pa at 20-25℃
• FEMA: 2885 | 3-PHENYL-1-PROPANOL
• refractive index: n20/D 1.526(lit.)
• Fp: 229 °F
• storage temp.: Sealed in dry,Room Temperature
• solubility: 0.1g/l insoluble
• pka: 15.04±0.10(Predicted)
• form: Liquid
• color: Clear colorless
• Odor: at 100.00 %. sweet spicy cinnamyl mignonette hyacinth balsam
• Odor Type: balsamic
• biological source: synthetic
• Water Solubility: 10.3 g/L (20 ºC)
• JECFA Number: 636
• BRN: 1857542
• Major Application: flavors and fragrances
• Cosmetics Ingredients Functions: FRAGRANCE PERFUMING SOLVENT
• InChI: 1S/C9H12O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,10H,4,7-8H2
• InChIKey: VAJVDSVGBWFCLW-UHFFFAOYSA-N
• SMILES: OCCCc1ccccc1
• LogP: 1.6-2.06 at 35℃
• CAS DataBase Reference: 122-97-4(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenylpropanol(122-97-4)
• EPA Substance Registry System: Benzenepropanol (122-97-4)

Safety Information

• Hazard Codes: Xi
• Risk Statements: 36/37/38-36/38-R36/38
• Safety Statements: 26-37/39-S37/39-S26
• WGK Germany: 1
• RTECS: UB8970000
• TSCA: TSCA listed
• HS Code: 29062900
• Storage Class: 8A - Combustible corrosive hazardous materials
• Hazard Classifications: Eye Dam. 1 Skin Corr. 1B
• Hazardous Substances Data: 122-97-4(Hazardous Substances Data)
• Toxicity: rabbit,LD50,skin,5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 17, Pg. 893, 1979.

3-Phenyl-1-propanol Usage And Synthesis

Chemical properties

Colorless viscous liquid with a sweet scent of flowers and sweetmeat and the flavor of fresh fruit after dilution. Its boiling point is at 236 °C, flash point at 109 °C. Soluble in ethanol, propylene glycol and most of the non-volatile oil, insoluble in glycerol and mineral oil, slightly soluble in water (1: 300).
Natural 3-Phenyl-1-propanol can be found in strawberries, Styrax cream, benzoin cream, tea, Peru Balsam, Cassia leaf oil, cinnamon oil and so on.

Uses

(1) Temporarily allowed as food flavouring agent in GB 2760-1996. Mainly used in the preparation of essence of peach, apricot, plum, watermelon, strawberry and nuts like walnut and hazel.
(2) Mainly used in the preparation of essence and medicine.
An intermediate of proformiphen (a central skeletal muscle relaxant)
Temporarily allowed as food flavouring agent in GB 2760-1996.
It has a sweet scent of flowers and sweetmeat and a pleasant flavor of fresh fruit after dilution
Natural 3-Phenyl-1-propanol can be found in strawberries, Styrax cream, benzoin cream, tea, Peru Balsam, Cassia leaf oil, cinnamon oil and so on.
(3) As a medicine, it can be applied to Cholecystitis, cholangitis, cholelithiasis, biliary postoperative syndrome, hypercholesterolemia, etc.
(4) Mainly used in the preparation of essence and medicine.
An intermediate of proformiphen, a central skeletal muscle relaxant.
As an antiputrefactiva in cosmetic in combination with piperonal or pepper, 3-Phenyl-1-propanol has a mold resistance on germ and mycete, along with a natural fragrance.
3-Phenyl-1-propanol or its ester derivatives can be used as flavor constituents of flowers such as lilac, hyacinth and keiskei for its aromatic vinegar.

content analysis

Total alcohol method (OT-5)Sample amount : l g,  Equivalent Factor (f) = 68.10.
nonpolar column method of gas chromatography (GT-10-4)

toxicity

GRAS(FEMA).
LD502300mg/kg (Rats oral).

Security utilization limitation

FEMA(mg/kg)：0.73 in soft drinks； 1.4 in cold drink； 2.8 in sweets； 3.3 in  baked food； 4.3 in gum confection； 5.0 in liquor. WHO Class II /moderate toxicity
Moderate limit (FDA§172．515，2000).

Production Method

(1) the catalytic hydrogenation of ethyl cinnamate.
The hydrogenation reaction is conducted in autoclave with chromium-copper-barium catalyst at 200℃ and 20MPa for 5-9h. The filtrate obtained after cooling and filtration is extracted by diethyl ether.  After the recycling of diethyl ether, reduced pressure distillation of the extracting solution is conducted to collect the fraction of 110-112℃（1.06kPa）, which is the finished product. The yield is about 85%.
Grignard reaction of benzyl chloride and oxirane, followed by the hydrolysis with sulfuric acid to obtain 3-Phenyl-1-propanol. The yield is about 65-70%。
(2) The hydrogenation of peruvin or cinnamaldehyde.

Standard for Maximum Allowable Amount

food additives: phenylpropanol
allowable usage:food
function of additives:Food flavouring
maximum allowable amount of usage (g/kg): The essence ingredients used in shall not exceed the maximum permissible usage and residues allowed in GB 2760.
maximum allowable amount of residue（g/kg）: The essence ingredients used in shall not exceed the maximum permissible usage and residues allowed in GB 2760.

Chemical Properties

CLEAR COLOURLESS LIQUID

Chemical Properties

3-Phenyl-1-propanol occurs both in freeand esterified forms in resins and balsams (e.g., benzoe resin and Peru balsam). Ithas been identified in fruits and cinnamon.
Hydrocinnamic alcohol is a slightly viscous, colorless liquid with a floralbalsamicodor, slightly reminiscent of hyacinths. Esterification with aliphaticcarboxylic acids is important because it leads to additional fragrance and flavormaterials.
Hydrocinnamic alcohol is prepared by hydrogenation of cinnamaldehyde. Amixture of hydrocinnamic alcohol and the isomeric 2-phenylpropanol can beobtained from styrene by a modified oxo synthesis. The two isomers can beseparated by distillation.
Hydrocinnamic alcohol is used in blossom compositions for balsamic and orientalnotes.

Chemical Properties

3-Phenyl-1-propanal has a characteristic sweet, hyacinth-mignonette odor. It has a sweet and pungent taste suggestiveof apricot.

Occurrence

Reported found in storax, Sumatra benzoin, tea, Peru balsam, passion fruit, strawberry, bilberry, high bushblueberry, European cranberry, guava peel, fresh blackberry, heated blackberry, rum, white wine, shitake, matsutake, peated malt,loquat, sapodilla fruit and crownberry.

Uses

3-Phenyl-1-propanol is used as a reagent in the synthesis of Dihydrocinnamyl Cilnidipine (D448605) and is a potent aroma biotransformation product.

Uses

Preservative in cosmetics - This alcohol a natural fragrance with antimicrobial properties against bacteria and molds. It is used in combination with Heliotropin or Piperonal as a preservative for cosmetic products.

Definition

ChEBI: 3-Phenyl-1-propanol is a monocyclic arene.

Preparation

By hydrogenation of either cinnamic aldehyde or cinnamic alcohol.

Taste threshold values

Taste characteristics at 20 ppm: spicy, cinnamon, balsamic, fruity, winy and honey-like with floral nuances.

Synthesis Reference(s)

Canadian Journal of Chemistry, 57, p. 2522, 1979 DOI: 10.1139/v79-404
Tetrahedron Letters, 32, p. 1321, 1991 DOI: 10.1016/S0040-4039(00)79656-0
Chemical and Pharmaceutical Bulletin, 24, p. 1059, 1976 DOI: 10.1248/cpb.24.1059

General Description

3-Phenyl-1-propanol is a fragrance ingredient.

Flammability and Explosibility

Not classified

3-Phenyl-1-propanol Preparation Products And Raw materials

• Raw materials: trans-Cinnamaldehyde-->CINNAMIC ALCOHOL-->Ethyl cinnamate-->1-Naphthalenemethanol-->5-PHENYL-1-PENTANOL-->6-PHENYL-1-HEXANOL-->Methyl cinnamate-->8-PHENYL-1-OCTANOL-->7-PHENYL-1-HEPTANOL-->4-Phenylbutanol-->3-Phenylpropionic acid methyl ester-->3-Phenyl-2-propen-1-ol-->Phenylacetylene-->carbon monoxide
• Preparation Products: Phenprobamate-->3-PHENYLPROPYL ACETATE-->Phenylpropyl aldehyde-->Cyclohexanecarboxylic acid, 3-phenylpropyl ester