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サリチルアルデヒド

Salicylaldehyde

HCID 6998
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
27761-48-4
標準SMILES
O=Cc1ccccc1O
InChIKey
SMQUZDBALVYZAC-UHFFFAOYSA-N
分子式
C7H6O2
平均分子量
122.12 g/mol
単同位体質量
122.03677943

概要

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

名称と識別子

優先名称
Salicylaldehyde
IUPAC
2-hydroxybenzaldehyde
現地名
サリチルアルデヒド
英語名
Salicylaldehyde
分子式
C7H6O2
分子量
122.12

名称と別名

SALICYLALDEHYDE2-Hydroxybenzaldehyde90-02-8o-Hydroxybenzaldehydeo-Formylphenol2-FormylphenolSalicylalSalicylic aldehydeBenzaldehyde, 2-hydroxy-SalicyladehydeFEMA No. 3004DTXSID1021792
名称をさらに表示
サリチルアルデヒド2-ヒドロキシベンズアルデヒド(サリチルアルデヒド)サルチルアルデヒド2-ヒドロキシベンズアルデヒドサリチルアルデヒド 2-ヒドロキシベンズアルデヒド2-ヒドロキシベンゼンカルボアルデヒドo-ホルミルフェノール2-ホルミルフェノールo-ヒドロキシベンズアルデヒドsalicyaldehydeFEMA 30042-hydroxy-benzaldehydSALICYLALDEHYDalicylaldehydeBenzaldehyde,2-hydroxy-
17K64GZH20NSC-49178DTXCID001792CHEBI:16008NSC-83559NSC-83560NSC-83561NSC-83562

データベース識別子

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

物性

構造計算による物性補完中

XLogP
1.8
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
9
形式電荷
0
複雑度
101

実験および物理化学的性質

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

Fragrance Ingredient (Salicylaldehyde) -> IFRA transparency List

Fragrance

LogP · 3 件

log Kow = 1.81

1.81

1.62

Odor · 2 件

Bitter, almond-like odor

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

Taste · 2 件

Nut-like, coumarin flavor at low levels

Burning taste

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 4 件

1.1674 at 68 °F (USCG, 1999) - Denser than water; will sink

1.167 g/cu cm at 20 °C/4 °C

1.159-1.170

1.167 @25 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 6 件

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 · 1 件

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]

化学と産業

薬理情報

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

用途と製造

Uses · 4 件

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 · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 4 件

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 · 5 件

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%.

関連反応

634 件
反応記録を作成
HRID 1712 の反応式
HRID 1712反応物としてuspto-grants-1998_03
HRID 2756 の反応式
HRID 2756反応物としてuspto-grants-1998_03
HRID 7149 の反応式
HRID 7149反応物としてuspto-grants-2006_08
HRID 10350 の反応式
HRID 10350反応物としてuspto-grants-2006_08
HRID 16172 の反応式
HRID 16172反応物としてuspto-grants-2010_06
HRID 18944 の反応式
HRID 18944反応物としてuspto-grants-2010_06
HRID 21680 の反応式
HRID 21680反応物としてuspto-grants-1995_06
HRID 21894 の反応式
HRID 21894反応物としてuspto-grants-1995_06
1 / 80 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Flavoring Agents
EU Flavoring substances
ViscosityDynamic viscosity = 2.50X10-3 Pa.s at 25 °C
Color/Form · 3 件

Liquid

Colorless, oily liquid or dark-red oil

Colorless to straw, oily liquid

物理化学的性質

融点
1 · 1-2 °C (lit.)
沸点
197 °C · 197 °C (lit.)
比重(密度)
1.146 g/mL · 1.146 g/mL at 25 °C (lit.)
蒸気密度
4.2 · 4.2 (vs air)
蒸気圧
1 mm · 1 mm Hg ( 33 °C)
屈折率
20 · n20/D 1.573(lit.)
FEMA
3004 · 3004 | SALICYLALDEHYDE
闪点
170 °F · 170 °F
貯蔵温度
-20 °C · -20°C
溶解性
4.9 g/リットル · 4.9g/リットル
外見
液体
酸解離定数(Pka)
8.37 · 8.37(at 25℃)
色
クリアイエロー
PH
6 · 6-8 (H2O, 20℃)Not applicable
臭い (Odor)
ビターアーモンド
においのタイプ
薬用
由来生物
synthetic
水溶解度
わずかに溶ける
比熱容量
1.82 J/ · Cp(liquid): 1.82 J/(g·K), at 25℃
JECFA Number
897 · 897
Merck
14 · 14,8326
BRN
471388 · 471388
Henry's Law Constant
1.1 · 1.1×100 mol/(m3Pa) at 25℃, Ji et al. (2008)
Dielectric constant
13.9 · 13.9(20℃)
安定性
安定。可燃性。強塩基、強還元剤、強酸、強酸化剤とは相容れない。
化粧品成分の機能
香料
InChI
1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
InChIKey
SMQUZDBALVYZAC-UHFFFAOYSA-N
SMILES
Oc1ccccc1C=O
LogP
1.66 at · 1.66 at 25℃ and pH6.2-6.3
CAS データベース
90 · 90-02-8(CAS DataBase Reference)
NISTの化学物質情報
2 · Benzaldehyde, 2-hydroxy-(90-02-8)
EPAの化学物質情報
Salicylaldehyde (90-02-8)
化学的性質 · 1 件

化学的特性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.

FDA Requirements · 1 件

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.

Reactive GroupAldehydes
TSCA Requirements · 2 件

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 · 1 件

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.

Reactivity Profile · 1 件

SALICYLALDEHYDE is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
NFPA Hazard Classification · 3 件

0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

安全と保護具

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

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 · 1 件

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)
Disposal Methods · 2 件

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: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. 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 · 5 件

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.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition. No smoking. Take measures to prevent the build up of electrostatic charge.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

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.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Allowable Tolerances · 1 件

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.

Protective Action Criteria (PAC) · 3 件

1.6 [mg/m3]

17 [mg/m3]

100 [mg/m3]

Personal Protective Equipment (PPE) · 5 件

Wear goggles and self-contained breathing apparatus. (USCG, 1999)

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).

Skin protection: Handle with gloves.

Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

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).

毒性情報

Ecotoxicity Values · 5 件

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 · 3 件

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 · 1 件

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 · 1 件

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]
Ongoing Test Status · 1 件

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of November 16, 2017: http://actor.epa.gov/dashboard/]

Effluent Concentrations2-Hydroxybenzaldehyde was detected, but not quantified, in exhaust samples from 9 test fuels employed in an automobile under simulated city driving conditions(1).
Soil Adsorption/Mobility · 1 件

The Koc of 2-hydroxybenzaldehyde is estimated as 73(SRC), using a log Kow of 1.81(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-hydroxybenzaldehyde is expected to have high mobility in soil.

Natural Pollution Sources · 1 件

2-Hydroxybenzaldehyde has been identified as a constituent in various tissues and essential oils of several plant species(1). 2-Hydroxybenzaldehyde occurs in the flowers of Spirea ulmaria and in the essential oils of several plants of the genus Spirea, in the roots of Crepis foetida, in the fruits of Pinus avium, in the rind of Rauqolfia caffra, in the leaves of Ceanothus velutinus and in the essential oil of Cinnamonum cassia and tobacco leaves. 2-Hydroxybenzaldehyde has also been reported in pennyroyal, cinnamon bark, cassia leaf, cassia oil, pepperment oil, and mastic gum oil(2,3).

Atmospheric ConcentrationsURBAN/SUBURBAN: 2-Hydroxybenzaldehyde was detected in atmospheric samples collected from Niteroi City, RJ, Brazil, between January 9th and 14th, 2010, with a reported mean and maximum of 3.73 and 7.64 ug/m cu, respectively(1).
Human Toxicity Excerpts · 1 件

/CASE REPORTS/ Salicyl alcohol or 2-methylolphenol is a well-known allergen in phenol-formaldehyde resins and a strong sensitizer in guinea pigs. There is 1 previous report of allergic contact dermatitis from salicyl alcohol in aspen bark. We describe a second case with concomitant allergy to salicylaldehyde. 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). Weaker reactions were observed to bark extracts of rowan (Sorbus aucuparia), tea-leaved willow (Salix phylicifolia) and goat willow (Salix caprea). We analyzed salicyl alcohol and salicylaldehyde in the bark extracts and found the 2 chemicals in equal amounts, about 0.9 ug/mg in aspen bark and in lower concentrations in rowan and the willows. We did not find either of the chemicals in the test substance of balsam of Peru (Myroxylon pereirae). 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.

法規制情報

FDA Requirements · 1 件

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 · 2 件

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 · 1 件

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.

安全データ

F
8-10-23
wgk
2
tsca
TSCA listed
rtecs
VN5250000
ridadr
3082
毒性
MLD in rats (mg/kg): 900-1000 s.c. (Binet)
PRTR法
第一種指定化学物質
hs_code
29122990
risk_code
21/22-36/38-68-36/37/38-20/21/22-51-36-51/53-22
化審法
(3)-1183, (3)-2660
消防法
危険物第4類第三石油類(非水溶性)
hazard_code
Xn,N
safety_code
26-36/37-36/37/39-36-61-64-29/35
hazard_class
6.1(b)
packing_group
II
環境リスク評価
サリチルアルデヒド(90-02-8)
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Muta. 2Skin Irrit. 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
90-02-8(Hazardous Substances Data)

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.

Household Products · 2 件

Cosmetics product ingredient: o-Hydroxy-benzaldehyde (Salicylaldehyde)

Information on 1 consumer products that contain Salicylaldehyde in the following categories is provided:

Use Classification · 5 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 件

Fabricated Metal Product Manufacturing

Benzaldehyde, 2-hydroxy-: ACTIVE

応用分野 · 8 件

解説2-hydroxybenzaldehyde.C7H6O2(122.12).カッシア油,シモツケ科の植物精油中に存在するが,フェノールからライマー-ティーマン反応によって合成される.無色の芳香をもつ液体.融点1.6 ℃,沸点197 ℃.d204"1.167.n20D"1.5735.水に微溶,エタノール,エーテルに可溶.クマリンの合成原料,香料,分析試薬として用いられる.LD50 1000 mg/kg(ラット,皮下).森北出版「化学辞典(第2版)

用途合成原料、香料原料

用途香水,クマリンの合成原料,医薬?農薬中間体

用途サリチルアルデヒドは,芳香族アルデヒドの一つで、o(オルト)-ヒドロキシベンズアルデヒドともよばれている。カシア油などの植物精油中に含まれている。芳香をもつ無色の液体で、エタノール(エチルアルコール)、エーテルなどの有機溶媒と任意の割合で混じり合う。フェノールとクロロホルムとを水酸化ナトリウムの存在下で反応させると得られる。芳香をもっているので香料としても用いられるが、おもな用途はクマリンの合成原料である。

説明Salicylaldehyde (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.

天然物の起源Occurs 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.

一般的な説明Liquid; colorless or pale yellow; bitter almond odor. Sinks and mixes slowly in water.

使用用途サリチルアルデヒドは、種々の化学品の合成原料として利用されています。ダキン反応により過酸化水素を用いて酸化すると、カテコールが得られます。クロロ酢酸によるエーテル化と環化反応により、複素環化合物のベンゾフランを得ることも可能です。アミンと縮合させることで、キレート配位子であるサレンやサリチルアルドキシムも得られます。 そのほか、香料としても利用されます。具体的には、バターやカラメル、ナッツ、シナモン、フルーツ系のフレーバーなどです。

調製方法 · 2 件

製造方法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.

純化方法It is precipitated as the bisulfite addition compound by pouring the aldehyde slowly and with stirring into a 25% solution of NaHSO3 in 30% EtOH, then standing for 30minutes. The precipitate, after filtering at the pump, and washing with EtOH, is decomposed with aqueous 10% NaHCO3, and the aldehyde is extracted into diethyl ether, dried with Na2SO4 or MgSO4, and distilled, under reduced pressure. Alternatively, salicylaldehyde is precipitated as its Cu complex by adding it to warm, saturated aqueous Cu(OAc)2, shaking and standing in ice. The precipitate is filtered off, washed with EtOH, then Et2O, and decomposed with 10% H2SO4; the aldehyde is extracted into Et2O, dried and vacuum distilled. It was also purified by dry column chromatography on Kieselgel G [Nishiya et al. J Am Chem Soc 108 3880 1986]. The acetyl derivative has m 38-39o (from pet ether or EtOH) and b 142o/18mm, 253o/atm. [Beilstein 8 IV 176.] The oxime, [94-67-7] M 137.1, crystallises CHCl3/pet ether (b 40-60o) with m 57o [Beilstein 8 IV 203.]

上流・下流製品情報

上流原料

2-ヒドロキシ安息香酸o-クレゾールクロロホルム水酸化ナトリウム

下流製品

サリチルアルドキシム3-(2-ベンズイミダゾリル)-7-(ジエチルアミノ)クマリン2-メチルベンゾフランベンゾ[B]フラン-2-カルボン酸メチル2-エトキシベンズアルデヒドL-2-フェニルグリシン3-メチルクマリンクマリン5-(2-エトキシフェニル)-1-メチル-3-プロピル-1,6-ジヒドロ-7H-ピラゾロ[4,3-d]-7-ピリミジノンa copper chelate1-Benzofuran-2-carboxamide3-アセトアミドクマリンセフィキシムD-アロトレオニン[2R,(+)]-2-メトキシ-4H-1,3,2-ベンゾジオキサホスホリン-2-スルフィド2-ベンゾフランカルボン酸エチルアミオダロン1,3,3-トリメチルインドリノベンゾピリロスピラン5-クロロサリチルアルデヒド2-[3-[(1,1-ジメチルエチル)アミノ]-2-ヒドロキシプロピルオキシ]ベンゾニトリル4-ヒドロキシベンズアルデヒド2-(2-ホルミルフェノキシ)プロパン酸2-[(2,6-ジクロロベンジル)オキシ]ベンズアルデヒド1-ベンゾフラン-2-カルボニルクロリド2-ホルミルベンゾフラン6-メチルクマリン2,3-ベンゾフランo-アニスアルデヒド2-シアノフェノール3-アリル-2-ヒドロキシベンズアルデヒド

補足説明

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