Benzenepropanol

HCID 31234CAS 122-97-4

기본 정보

표준 SMILES
OCCCc1ccccc1
InChIKey
VAJVDSVGBWFCLW-UHFFFAOYSA-N
분자식
C9H12O
평균 분자량
136.19 g/mol
단동위원소 질량
136.088815

개요

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

이름 및 식별자

우선 이름
Benzenepropanol
IUPAC
3-phenylpropan-1-ol
현지명
페닐프로필 알코올
영어명
3-Phenyl-1-propanol
분자식
C9H12O
분자량
136.19

이름 및 동의어

3-PHENYL-1-PROPANOL3-Phenylpropan-1-ol122-97-4Benzenepropanol3-Phenylpropanol3-Phenylpropyl alcohol3-BenzenepropanolHydrocinnamic alcohol3-Phenyl-n-propanol1-Propanol, 3-phenyl-Benzylethyl alcoholgamma-Phenylpropanol
이름 더 보기
3-페닐프로판-1-올페닐프로필알코올페닐프로필알코올페닐프로판올3-페닐-1-프로판올PhenylpropanolPHENYL PROPYL ALCOHOLHYDROCINNAMYL ALCOHOLPhenylpropylFEMA 28853-phenyl-1-propanoAlverine Citrate Impurity B
1-Hydroxy-3-phenylpropaneDihydrocinnamal alcoholFEMA No. 2885DTXSID6041638U04IC2765CNSC-16942DTXCID4021638RefChem:916891

데이터베이스 식별자

CAS
122-97-4、1335-12-2、93842-54-7
PubChem CID
31234
DTXSID
DTXSID6041638
ChEMBL
CHEMBL1606391
ChEBI
CHEBI:88817
UNII
U04IC2765C
EC Number
204-587-6
Nikkaji
J44.158I

물성

구조 계산 물성

XLogP
1.9
극성 표면적
20.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
3
무거운 원자 수
10

실험 및 물리화학적 성질

PolymersOther Classes -> Alcohols and Polyols, Other
CosmeticsSolvent
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (3-Phenyl-1-propanol) -> IFRA transparency List
LogP · 3건

log Kow = 1.88

1.88

1.83

Odor · 3건

Floral odor

Blossomy-balsamic odor, slightly reminiscent of hyacinths

Sweet, hyacinth-mignonette odor

물리화학적 성질

녹는점
18 °C · −18 °C(lit.)
끓는 점
119 · 119-121 °C12 mm Hg(lit.)
밀도
1.001 g/mL · 1.001 g/mL at 20 °C(lit.)
증기압
1.13 · 1.13-25Pa at 20-25℃
FEMA
2885 · 2885 | 3-PHENYL-1-PROPANOL
굴절률
20 · n20/D 1.526(lit.)
화학적 성질 · 1건

3-Phenyl-1-propanol occurs both in free and esterified forms in resins and balsams (e.g., benzoe resin and Peru balsam). It has been identified in fruits and cinnamon. Hydrocinnamic alcohol is a slightly viscous, colorless liquid with a floralbalsamic odor, slightly reminiscent of hyacinths. Esterification with aliphatic carboxylic acids is important because it leads to additional fragrance and flavor materials. Hydrocinnamic alcohol is prepared by hydrogenation of cinnamaldehyde. A mixture of hydrocinnamic alcohol and the isomeric 2-phenylpropanol can be obtained from styrene by a modified oxo synthesis. The two isomers can be separated by distillation. Hydrocinnamic alcohol is used in blossom compositions for balsamic and oriental notes.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1996) of reports.

Danger

H314 (11.5%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P332+P317, P337+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1996 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

유해성 정보

Regulatory Information · 6건

Chemical: 1-Propanol, phenyl-

Chemical: Benzenepropanol

Regulation (EC) No 1831/2003 (amended)

Benzenepropanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenepropanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 21-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16763

Benzenepropanol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2건

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

IMAP assessments - 1-Propanol, phenyl-: Environment tier I assessment

Fire PotentialCombustible liquid
Hazards Summary · 1건

Another member of the benzene alkyl alcohols cluster demonstrates skin and eye irritation in experimental animals; Low toxicity in repeated-dose dermal study; No evidence of toxicity to reproductive organs; Moderate developmental toxicity in one study and high developmental toxicity in another (less well documented); [EPA ChAMP: Screening Level Hazard Characterization] A moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] Fragrance ingredient with positive human patch test results (2 of 218 patients), but insufficient data to classify as established contact allergen in humans; [EC: SCCS] A skin and strong eye irritant; [Sigma-Aldrich MSDS]

EPA Safer ChemicalChemical: 3-Phenylpropanol
NFPA Hazard Classification · 3건

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

안전 및 보호

Fire Fighting Procedures · 4건

Special hazards arising from the substance or mixture: Carbon oxides

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary.

Extinguishing Methods: alcohol resistant fire fighters foam.

Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 2건

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Do not let product enter drains.

Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Disposal Methods · 2건

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Preventive Measures · 2건

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Normal measures for preventive fire protection.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Personal Protective Equipment (PPE) · 4건

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Body Protection: Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Skin protection: Handle with gloves.

Eye/face protection safety: Use glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 71(SRC), determined from a structure estimation method(2), indicates that 3-phenylpropanol is expected to have high mobility in soil(SRC). Volatilization of 3-phenylpropanol from moist soil surfaces is not expected to be an important fate process(SRC) given a measured Henry's Law constant of <5.6X10-8 atm-cu m/mole(3). Even though the extrapolated vapor pressure is low environmentally at standard temperature and pressure, 0.0234 mm Hg at 25 °C(5), there is a detectable odor; therefore, 3-phenylpropanol may volatilize from dry soil(SRC). Utilizing the Zahn-Wellens test, 100% biodegradation was reached in 4 days(6) indicating that biodegradation is an important environmental fate procession soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 71(SRC), determined from a structure estimation method(2), indicates that 3-phenylpropanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a measured Henry's Law constant of <5.6X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 4.5(SRC), from its log Kow of 1.88(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Zahn-Wellens test, 100% biodegradation was reached in 4 days(7) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-phenylpropanol, which has an extrapolated vapor pressure of 0.0234 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-phenylpropanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.2X1-11 cu cm/molecule-sec at 25 °C(SRC) (that was derived using a structure estimation method(3). 3-Phenylpropanol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

3-Phenylpropanol was detected in the skin and pulp of Queen Anne's pocket melon (Cucumis melo var. dudaim (L.) Naudin) at respective concentrations of 365.3 and 216.5 ug/kg(1). 3-Phenylpropanol is reportedly found in heated blackberry, rum, and white wine(2).

Toxicity Summary · 1건

IDENTIFICATION AND USE: 3-Phenylpropanol is a colorless liquid. It smells like hyacinths and tastes similar to apricot. It occurs in many fruits and berries, cinnamon and some types of balsam. 3-Phenylpropanol occurs in tobacco smoke. 3-Phenylpropanol is typically used as a perfume for applications such as antiperspirants, creams-lotions, lipsticks, talcum powder, tablet soap, shampoo, hair conditioner, bath/shower gel, detergent powder, liquid detergent, fabric softener, candles, incense. Also used in blossom compositions for balsamic and oriental notes. It is not registered for current pesticide use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: In a multicenter study, 218 fragrance sensitive patients with proven contact dermatitis were patch tested. Reactions (0.9%) in fragrance sensitive patients were observed with 3-phenylpropanol at 5% in petrolatum. ANIMAL STUDIES: In rats dosed orally with 3-phenylpropanol at dose levels of 1.31, 2.56 and 5.0 g/kg/bw deaths occurred within the first 2 days. The clinical signs observed were slight lethargy and flaccid muscle tone. In a preliminary screen for an acute oral toxicity study, a 50% solution of 3-phenyl-1-propanol in corn oil was administered orally to 10 rats at a dose level of 5 g/kg bw, nine (9/10) rats died. In another study, rats were dosed orally with a 50% solution of 3-phenylpropanol in corn oil at dose levels of 1.47, 2.15, 3.16 and 4.64 g/ kg bw. One death occurred at 1.47 g/kg; and at 2.15 and at 4.64 g/kg. The clinical signs observed during the study were depression, hypopnea, ataxia and piloerection. Gross observations at necropsy revealed dark red areas in the lungs at the three lower doses and dark red lungs at the highest dose. In an irritation study in rabbits 3-phenylpropanol was applied for 24 hr under occlusion at dose levels of 2.5 and 5 g/kg. At 2.5 g/kg, moderate erythema and slight to moderate edema were observed. At 5 g/kg, moderate to severe erythema and moderate edema were observed. In another study in rabbits, 3-phenyl-1-propanol was applied for 24 hr under occlusion at 5 g/kg. Moderate to severe erythema, severe edema, scaling and necrosis were observed. A 0.5 mL aliquot of 3-phenylpropanol was applied to intact and abraded skin for 24 hr under occlusion. Moderate irritation was observed. Necrosis was also observed. No mutagenic or genotoxic activity in bacteria and mammalian cell line assay was found.

Average Daily IntakeThe dermal systemic exposure to 3-phenylpropanol in cosmetic products is estimated as 0.0204 mg/kg-day(1).
Plant Concentrations · 2건

3-Phenylpropanol is reportedly found in bilberry (Vaccinium myrtillus L.), high bush blueberry (Vaccinium corymbosumL.), European cranberry (Vaccinium oxycoccus L.), guava fruit (Psidium guajava L.), guava peel, fresh blackberry, shittake (Lentinus edodes Sing.), matsutake (Tricholoma matsutake), peated malt, loquat (Eriobotyra japonica Lindl.), sapodilla fruit (Archras sapota L.), and crowberry (Empetrum nigrum Coll.)(1).

3-Phenylpropanol detections in plants(1).[Table#8251]

Effluent Concentrations3-Phenylpropanol was detected in wastewater effluents from the rum and timber products industries(1).

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
UB8970000
독성
rabbit,LD50,skin,5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 17, Pg. 893, 1979.
HS 번호
29062900
risk_code
36/37/38-36/38-R36/38

화학 및 산업

약리 정보

Absorption, Distribution and Excretion · 1건

An in vitro percutaneous absorption study of 3-phenyl-1-propanol, across human skin was conducted using a diffusion cell. Skin samples, approximately 280 um thick, were obtained from cosmetic surgical human abdominal skin. The dermatomed skin samples were fixed in 4% formaldehyde, embedded in paraffin. 3-Phenyl-1-propanol (5.0 mg/mL, working concentration) was dissolved in buffer solution at a concentration equivalent to approximately 75% of its solubility in that medium. The solution was used to fill the donor compartment while the receptor compartment was filled with pH 7.4 buffer solution. The experiments were carried out at 37 °C. The cells were immersed in a thermostatically regulated water bath. Assay duration was 7 hr. Receptor compartment sampling was carried out every 30 min and the extracted samples were replaced with the buffer solution. Samples were analyzed by gas chromatograph with a flame ionization detector. The mean permeability coefficient for 3-phenyl-1-propanol was reported to be 52.35 +/- 4.98 Kp[cm/hour] and the flow value was 1.18 +/- 0.11 J[mg/hr].

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

Used as a flavoring agent; [FDA]

For 3-phenyl-1-propanol (USEPA/OPP Pesticide Code: 040511) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Perfumery, flavoring, laboratory reagent

Used in blossom compositions for balsamic and oriental notes ... Esterification with aliphatic carboxylic acids is important because it leads to additional fragrance and flavor compounds.

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.

For more Uses (Complete) data for 3-Phenylpropanol (6 total), please visit the HSDB record page.

U.S. Production · 2건

2023: 50,000 - <75,000 lb

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzenepropanol. National Production Volume: Withheld.

Consumer UsesSolvent
Industry UsesFlavoring and nutrient
Methods of Manufacturing · 2건

By hydrogenation of either cinnamic aldehyde or cinnamic alcohol.

Hydrocinnamic alcohol is prepared by hydrogenation of cinnamaldehyde. A mixture of hydrocinnamic alcohol and the isomeric 2-phenylpropanol can be obtained from styrene by a modified oxo synthesis. The two isomers can be separated by distillation.

Household ProductsInformation on 9 consumer products that contain 3-Phenylpropanol in the following categories is provided:
응용 분야 · 3건

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

용도3-Phenyl-1-propanol is used as a reagent in the synthesis of Dihydrocinnamyl Cilnidipine (D448605) and is a potent aroma biotransformation product.

일반 설명3-Phenyl-1-propanol is a fragrance ingredient.

제조 방법

By hydrogenation of either cinnamic aldehyde or cinnamic alcohol.

공급사50 곳

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