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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 74.8
실험 및 물리화학적 성질
LogP
log Kow = 1.88
1.88
1.83
Odor
Floral odor
Blossomy-balsamic odor, slightly reminiscent of hyacinths
Sweet, hyacinth-mignonette odor
Taste
Sweet and pungent taste suggestive of apricot
Spicy, cinnamon, balsamic, fruity, winey and honey-like with floral nuances
Density
0.995 g/cu cm at 25 °C
0.993-1.002
Color/Form
Colorless liquid
Slightly viscous, colorless liquid
Solubility
In water, 5,680 mg/L at 25 °C
Soluble in carbon tetrachloride; miscible with ethanol, ether
Soluble in fixed oils, propylene glycol; insoluble in glycerin
5.68 mg/mL at 25 °C
slightly soluble in water; soluble in oils
miscible (in ethanol)
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.)
- 인화점
- 229 °F · 229 °F
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 0.1 g/l · 0.1g/l 불용성
- 산도 계수 (pKa)
- 15.04 · 15.04±0.10(Predicted)
- 물리적 상태
- 액체
- 색상
- 무색의
- 냄새
- 100 %에서 · 100.00%에서. 달콤하고 매콤한 신나밀 미뇨네트 히아신스 발삼
- 냄새 유형
- 발사믹
- 생물학적 소스
- synthetic
- 수용성
- 10.3 g/L · 10.3 g/L (20 ºC)
- JECFA Number
- 636 · 636
- BRN
- 1857542 · 1857542
- Henry's Law Constant
- 1.8 · 1.8×102 mol/(m3Pa) at 25℃, Altschuh et al. (1999)
- 주요 응용
- 향료 및 향
- 화장품 원료 기능
- 향기향수용제
- 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 · 1.6-2.06 at 35℃
- NIST
- 3 · 3-Phenylpropanol(122-97-4)
- EPA
- Benzenepropanol (122-97-4)
화학적 성질
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
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
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
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
IMAP assessments - 1-Propanol, phenyl-: Environment tier I assessment
Hazards Summary
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]
NFPA Hazard Classification
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.
Toxic Combustion Products
Special hazards arising from the substance or mixture: Carbon oxides
When heated to decomposition it emits toxic fumes.
안전 및 보호
Fire Fighting Procedures
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.
Cleanup Methods
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
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
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)
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
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
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
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.
Plant Concentrations
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]
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 3-phenylpropanol can be estimated to be 71(SRC). According to a classification scheme(2), this estimated Koc value suggests that 3-phenylpropanol is expected to have high mobility in soil.
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ Closed patch tests were conducted on 82 patients with 0.05- 0.5% 3-phenyl-1-propanol in a base cream or in 99% ethanol. Patches consisted of a piece of 1.0 sq cm lint with a 2.0 sq cm cellophane disc placed on the lint and covered with a 4.0 sq cm plaster. Patches were applied to the back, the forearm and the inside of the upper arm for 24-48 hr. Reactions were read 30 min after patch removal. No reactions were observed.
/HUMAN EXPOSURE STUDIES/ In a multicenter study, 218 fragrance sensitive patients with proven contact dermatitis were patch tested with various fragrance materials according to internationally accepted criteria. Reactions (0.9%) were observed with 5% 3-phenyl-1-propanol in petrolatum.
/HUMAN EXPOSURE STUDIES/ A maximization test was carried out with 8% 3-phenyl-1-propanol in petrolatum on 25 healthy (17 female/8 male) volunteers. Application was under occlusion to the same site on the forearms or backs of all subjects for five alternate-day 48 hr periods. Patch sites were pretreated for 24 hr with 2.5% aqueous sodium lauryl sulfate (SLS) under occlusion. Following a 10 day rest period, challenge patches were applied to fresh sites for 48 hr under occlusion. Challenge sites were pretreated with aqueous SLS. Reactions to the challenge were read at patch removal and 24 hr thereafter. No sensitization reactions were observed.
/HUMAN EXPOSURE STUDIES/ A human repeated insult patch test was conducted on 50 male and female volunteers. Induction patches with 3-phenyl-1-propanol at 4% in petrolatum, were applied for 24 hr under occlusion to the upper arm 3 days a week (Monday/ Wednesday/ Friday) for a total of 15 applications. A 2 week rest period followed the last induction application, followed by a 24 hr challenge patch at the same skin site. The challenge site was read at patch removal, and 24 and 48 hr thereafter. No reactions were produced.
/HUMAN EXPOSURE STUDIES/ Irritation was evaluated during the induction phase of a human repeated insult patch test (HRIPT) which was conducted on 50 healthy volunteers. 3-Phenyl-1-propanol at 4% in petrolatum was applied to a 3 sq cm patch, which was then applied to the upper arm of each volunteer for 24 hr under occlusion. A total of 15-24 hr applications were made. Reactions were read at patch removal. No irritation was observed.
Artificial Pollution Sources
3-Phenylpropanol's production and use in the synthesis of flavor and fragrance compounds(1), as a flavoring agent in foods(2) and as a preservative in cosmetics(3) may result in its release to the environment through various waste streams(SRC). Its use as a perfume(1,2) may result in its direct result to the environment(SRC). 3-Phenylpropanol has been identified as a component of tobacco smoke(4).
Environmental Biodegradation
AEROBIC: Using the static Zahn-Wellens test, 3-phenylpropanol was determined to be biodegradable based on 100% biodegradation over a 4-day incubation period(1). 3-Phenylpropanol had a 5-day theoretical BOD of 76.8% using a sewage inoculum and a respirometric dilution method(2).
Environmental Bioconcentration
An estimated BCF of 4.5 was calculated in fish for 3-phenylpropanol(SRC), using a log Kow of 1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
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
- hazard_code
- Xi
- safety_code
- 26-37/39-S37/39-S26
- 기존화학 물질
- KE-02588
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- 스토리지 클래스
- 8A - Combustible corrosive hazardous materials
- 유해 물질 데이터
- 122-97-4(Hazardous Substances Data)
화학 및 산업
약리 정보
Absorption, Distribution and Excretion
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].
용도 및 제조
Uses
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
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.
Methods of Manufacturing
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.
Use Classification
EPA Safer Chemical Functional Use Classes -> Defoamers
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Benzenepropanol: ACTIVE
1-Propanol, phenyl-: ACTIVE
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
관련 반응
연결된 노트
불러오는 중…