살리실 알데히드

Salicylaldehyde

HCID 6998CAS 27761-48-4

기본 정보

표준 SMILES
O=Cc1ccccc1O
InChIKey
SMQUZDBALVYZAC-UHFFFAOYSA-N
분자식
C7H6O2
평균 분자량
122.12 g/mol
단동위원소 질량
122.03677943

개요

Liquid; colorless or pale yellow; bitter almond odor. Sinks and mixes slowly in water. (USCG, 1999)

이름 및 식별자

우선 이름
Salicylaldehyde
IUPAC
2-hydroxybenzaldehyde
현지명
살리실 알데히드
영어명
Salicylaldehyde
분자식
C7H6O2
분자량
122.12

이름 및 동의어

SALICYLALDEHYDE2-Hydroxybenzaldehyde90-02-8o-Hydroxybenzaldehydeo-Formylphenol2-FormylphenolSalicylalSalicylic aldehydeBenzaldehyde, 2-hydroxy-SalicyladehydeFEMA No. 3004DTXSID1021792
이름 더 보기
살리실알데히드살리실알데하이드O-하이드록시벤즈알데히드2-하이드록시벤즈알데히드살리실알2-포름일salicyaldehydeFEMA 30042-hydroxy-benzaldehydSALICYLALDEHYDalicylaldehydeBenzaldehyde,2-hydroxy-
17K64GZH20NSC-49178DTXCID001792CHEBI:16008NSC-83559NSC-83560NSC-83561NSC-83562

데이터베이스 식별자

CAS
27761-48-4、28777-87-9、90-02-8
PubChem CID
6998
DTXSID
DTXSID1021792
ChEMBL
CHEMBL108925
ChEBI
CHEBI:16008
UNII
17K64GZH20
EC Number
201-961-0
Nikkaji
J10.607K、J3.808.468B

물성

구조 계산 물성

XLogP
1.8
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
9

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Benzaldehydes
CosmeticsCosmetics ingredient -> Fragrance
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Fragrances · 2건

Fragrance Ingredient (Salicylaldehyde) -> IFRA transparency List

Fragrance

LogP · 3건

log Kow = 1.81

1.81

1.62

Odor · 2건

Bitter, almond-like odor

Pungent, irritating odor similar to benzenaldehyde, acetophenone, and nitrobenzene, but with phenolic notes

물리화학적 성질

녹는점
1 · 1-2 °C (lit.)
끓는 점
197 °C · 197 °C (lit.)
밀도
1.146 g/mL · 1.146 g/mL at 25 °C (lit.)
증기 밀도
4.2 · 4.2 (vs air)
증기압
1 mm · 1 mm Hg ( 33 °C)
굴절률
20 · n20/D 1.573(lit.)
화학적 성질 · 1건

Salicylaldehyde is a colourless to yellow oily liquid with a pungent, irritating, bitter, almond-like odor similar to benzaldehyde, acetophenone and nitrobenzene, but with phenolic notes. It has a nut-like, coumarin flavor at low levels. slightly soluble in water, soluble in ethanol and ether. It turns purple in case of ferric chloride.

안전 및 규제

GHS 분류

GHS Classification · 6건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3872 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: Benzaldehyde, 2-hydroxy-

Hazard Traits - Fragrance Allergen

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzaldehyde, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 2-hydroxy- 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: 28-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5715

2-Hydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible. Can react with oxidizing materials. (USCG, 1999)
Fire PotentialFlamable when exposed to heat or flame.
Health HazardsLIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)
Hazards Summary · 1건

A skin and eye irritant; [CAMEO] A skin irritant; [eChemPortal: ERMA] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] An irritant; Can be absorbed through skin; [MSDSonline]

FDA Requirements · 1건

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Salicylaldehyde is included on this list.

안전 및 보호

Fire FightingExtinguish with water fog, alcohol foam, CO2 or dry chemical. (USCG, 1999)
First AidCall a doctor.
Fire Fighting Procedures · 4건

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

To fight fire, use alcohol foam, spray, mist, dry chemical.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Cleanup Methods · 1건

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

Nonfire Spill ResponseAvoid contact with liquid or vapor. Keep people away. Wear goggles and self-contained breathing apparatus. Stop discharge if possible. Isolate and remove discharged material. Notify local health and pollution control agencies. (USCG, 1999)

독성 정보

Ecotoxicity Values · 5건

EC50; Species: Scenedesmus subspicatus (Green Algae) exponential growth phase; Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 12000 ug/L for 48 hr; Effect: population, decreased biomass /formulation/

EC50; Species: Scenedesmus subspicatus (Green Algae) exponential growth phase; Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 11000 ug/L for 72 hr; Effect: population, decreased biomass /formulation/

EC50; Species: Scenedesmus subspicatus (Green Algae) exponential growth phase; Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 12000 ug/L for 96 hr; Effect: population, decreased biomass /formulation/

EC50; Species: Scenedesmus subspicatus (Green Algae) exponential growth phase; Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 22000 ug/L for 72 hr; Effect: decreased population /formulation/

For more Ecotoxicity Values (Complete) data for 2-Hydroxybenzaldehyde (18 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a log Kow of 1.81(2) and a regression-derived equation(3), indicates that 2-hydroxybenzaldehyde is expected to have high mobility in soil(SRC). Volatilization of 2-hydroxybenzaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 5.93X10-1 mm Hg(4), and water solubility, 1.7X10+4 mg/L(5). 2-Hydroxybenzaldehyde has a vapor pressure close to one and exists as a liquid under environmental conditions; therefore, 2-hydroxybenzaldehyde may volatilize from dry soil(SRC). Utilizing an inherent biodegradation test complete degradation was observed indicating that biodegradation is an important environmental fate process in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 73(SRC), determined from a log Kow of 1.81(2) and a regression-derived equation(3), indicates that 2-hydroxybenzaldehydeis not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 5.6X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 5.93X10-1 mm Hg(5), and water solubility, 1.7X10+4 mg/L(6). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 5 and 57 days, respectively(SRC). According to a classification scheme(8), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing an inherent biodegradation test complete degradation was observed indicating that biodegradation is likely an important environmental fate process in water(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-hydroxybenzaldehyde, which has a vapor pressure of 5.93X10-1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-hydroxybenzaldehyde 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 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Hydroxybenzaldehyde contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1건

2-Hydroxybenzaldehyde has been reported in grapes, tomato, baked potato, parmesan cheese, butter, milk powder, roasted chicken, beer, rum, Japanese whiskey, sherry, coffee, tea, soybean, mushroom, buckwheat, Bourbon vanilla, Chinese quince, Muscat grape, and vanilla(1). 2-Hydroxybenzaldehyde has been identified, but not quantified, as a volatile constituent of baked potatoes(2).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity Summary · 1건

IDENTIFICATION AND USE: Salicylaldehyde is a liquid. It is used in analytical chemistry, perfumery (violet), synthesis of coumarin, as an auxiliary fumigant, and flavoring. HUMAN STUDIES: An elk researcher who had handled leaves from various trees presented with eczema of the hands, face, flexures, trunk and extremities. Patch testing showed sensitivity to salicyl alcohol, salicylaldehyde, balsam of Peru (Myroxylon pereirae resin), aspen wood dust and an extract prepared from the bark of aspen (Populus tremula). Besides salicyl alcohol, salicylaldehyde is also recommended to be used to screen for contact allergy to aspen. Both of these chemicals should be tested in forest workers in areas where aspen is growing. ANIMAL STUDIES: Salicylaldehyde fed to male rats for 10 days or more caused an increase in the number and size of hepatic and renal microbodies and caused fibrillar material to appear. The drug did not cause fibrillar material to appear in hepatic microbodies of mice or microbodies of transplantable rat hepatomas. Salicylaldehyde evoked a hypocalcemia in rats and mice. Salicylaldehyde and its acetyl derivatives are all less potent analgesics and antinflammatory agents in rodents than salicylic acid and aspirin.

Plant Concentrations2-Hydroxybenzaldehyde detections in plants(1).[Table#2034]

규제 정보

FDA Requirements · 1건

Synthetic flavoring substances and adjuvants may be safely used in food in accordance with the following conditions. (a) They are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice. (b) They consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part. Salicylaldehyde is included on this list.

TSCA Requirements · 2건

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzaldehyde, 2-hydroxy- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

FIFRA Requirements · 1건

Residues of salicylaldehyde are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: Penetration aid. Limit: Not to exceed 14% by weight of pesticide formulation.

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
VN5250000
ridadr
3082
독성
MLD in rats (mg/kg): 900-1000 s.c. (Binet)
HS 번호
29122990

화학 및 산업

약리 정보

Absorption, Distribution and ExcretionAt fixed cosubstrate levels of salicylaldehyde, enzyme kinetics showed substrate inhibition effects.
Cellular LocationsCytoplasm

용도 및 제조

Uses · 4건

Used in perfumes, flavoring agents, auxiliary fumigants, reagents, and gasoline additives; Used to make coumarin and chelates; [HSDB] Important derivative of benzaldehyde; Occurs naturally in cassia oil; [Ullmann]

In perfumery

Reported uses (ppm):

Analytical chemistry, perfumery (violet), synthesis of coumarin, auxiliary fumigant, flavoring.

U.S. Exports · 2건

(1972) No Data

(1975) No Data

U.S. Imports · 2건

(1972) No Data

(1975) No Data

U.S. Production · 4건

2023: 1,764 lb

(1972) 2.03X10+9 GRAMS

(1975) 2.10X10+9 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: o-Hydroxybenzaldehyde:

Industry UsesCorrosion inhibitor
Methods of Manufacturing · 5건

One industrial process starts with phenol and forms 2-hydroxybenzyl alcohol (saligenin) by reacting triphenyl metaborate with formaldehyde. The alcohol is catalytically oxidized in air to give 2-hydroxybenzaldehyde. It is more economical to react phenol with formaldehyde in the presence of alkaline catalysts and in the absence of boric acid. The yield is approximately 85%. The ratio of 2-hydroxybenzyl alcohol to 4-hydroxybenzyl alcohol can be altered by varying the catalyst. The oxidation of the hydroxybenzyl alcohols is carried out in an aqueous solution with a platinum-lead-carbon catalyst and gives the corresponding hydroxybenzaldehydes in yields of more than 98%.

The best known process /for the manufacture of 2-hydroxybenzaldehyde/ is based on the Reimer-Tiemann reaction, in which phenol is reacted with chloroform in the presence of an aqueous alkali. Moderate yields of 2-hydroxy- and 4-hydroxybenzaldehyde are obtained in a ratio of about 85:15. The use of aqueous methanol as a reaction medium improves the yield, especially that of 4-hydroxybenzaldehyde. According to a modern variation of the Reimer-Tiemann reaction, the process is carried out in the absence of water. An alkali-metal phenolate reacts with chloroform and a suspension of an alkali-metal hydroxide in an inert organic solvent.

2-Hydroxybenzaldehyde can also be produced by electrolytic reduction of salicylic acid on a rotating amalgam cathode and by catalytic reduction of a salicylic acid halide.

Made by heating sodium phenolate and chloroform with NaOH.

Synthesis: From phenol, chloroform, and alkali according to Reimer-Tiemman method (1876); starting material for mfr of coumarin.

응용 분야 · 3건

개요Salicylaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless or pale yellow liquid with a bitter almond odor and a burning taste. It is soluble in alcohol, benzene, and ether, and very slightly soluble in water. Salicylaldehyde is found in shrubs of the genus Spiraea and is usually produced from phenol by the action of chloroform in the presence of an alkali base. It is used in the production of coumarin, saligenin, and salicylaldoxime (an important analytical reagent), and also in analytical chemistry—for example, to detect hydrazine. Besides, salicylaldehyde is a key precursor to various chelating agents and a flavouring ingredient.

출처Occurs frequently in nature; in the flowers of Spirea ulmaria and other Spireae, in the roots of Crepis foetida L., in the fruits of Pinus avium, in the rind of Rauqolfia caffra, in the leaves of Ceanothus velutinus and in the essential oil of Cinnamomum cassia and of tobacco leaves. Also reported found in grapes, tomato, baked potato, cinnamon bark, cassia leaf, peppermint oil, pennyroyal oil, parmesan cheese, butter, milk powder, roasted chicken, beer, rum, Japanese whiskey, sherry, coffee, tea, soybean, mushroom, buckwheat, Bourbon vanilla, Chinese quince, Muscat grape, vanilla and mastic gum oil.

일반 설명Liquid; colorless or pale yellow; bitter almond odor. Sinks and mixes slowly in water.

제조 방법

Salicylaldehyde is synthesized from phenol, chloroform, and alkali according to the Reimer–Tiemman method, which was developed in 1876. starting material for the manufacture of coumarin.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

추가 설명

정의ChEBI: Salicylaldehyde is a hydroxybenzaldehyde carrying a hydroxy substituent at position 2. It has a role as a nematicide and a plant metabolite.

관련 반응

634건

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