n-オクタナール

Octanal

HCID 454CAS 124-13-0

基本情報

標準SMILES
CCCCCCCC=O
InChIKey
NUJGJRNETVAIRJ-UHFFFAOYSA-N
分子式
C8H16O
平均分子量
128.21 g/mol
単同位体質量
128.12011513

概要

N-octylaldehyde is a colorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125 °F. Used in making perfumes and flavorings.

名称と識別子

優先名称
Octanal
IUPAC
octanal
現地名
n-オクタナール
英語名
Octanal
分子式
C8H16O
分子量
128.21

名称と別名

Octanal124-13-0CaprylaldehydeCaprylic aldehyden-Octanal1-octanaln-Octyl aldehyden-Caprylaldehyden-OctaldehydeOctanaldehyden-OctylalAldehyde C-8
名称をさらに表示
n-オクタナールカプリルアルデヒドオクチルアルデヒド1-オクタノンアンチフォームLFオクタナールn-オクチルアルデヒドn-オクタアルデヒドn-オクタンアルデヒド1-オクタナール1‐オクタナールオクタナール, 1000 µg/mL in Methanolオクタナール, 98%オクタナ-ルオクタン-1-アールオクタン-1-オンOCTYL ALDEHYDEFEMA 2797ORANGE ALDEHYDENatural Doctanal
Octanoic aldehydeOctaldehydeC-8 aldehydeOCTYLALDEHYDE1-Octylaldehyde1-Octaldehyde1-CaprylaldehydeOctanal, tech.

データベース識別子

CAS
124-13-0、9006-52-4
PubChem CID
454
DTXSID
DTXSID3021643
ChEMBL
CHEMBL18407
ChEBI
CHEBI:17935
UNII
XGE9999H19
EC Number
204-683-8、618-432-9
Nikkaji
J2.504F

物性

構造計算による物性

XLogP
2.7
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
6
重原子数
9

実験および物理化学的性質

Chemical ClassesOther Classes -> Aldehydes
LipidsFatty Acyls [FA] -> Fatty aldehydes [FA06]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Octanal) -> IFRA transparency List
LogP · 2 件

log Kow = 3.5 at pH 6.9 (by HPLC)

2.53

Odor · 3 件

Strong, fruity odor

Fatty, citrus, honey odor on dilution

Pungent odor; citrus-like on dilution

物理化学的性質

融点
12 · 12-15 °C(lit.)
沸点
171 °C · 171 °C(lit.)
比重(密度)
0.822 g/mL · 0.822 g/mL at 20 °C
蒸気圧
2 mm · 2 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.421(lit.)
FEMA
2797 · 2797 | OCTANAL
化学的性質 · 1 件

化学的特性Octanal occurs in several citrus oils, for example, orange oil. It is a colorless liquid with a pungent odor, which becomes citrus-like on dilution. Octanal is used in perfumery in low concentrations, in eau de cologne, and in artificial citrus oils.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1971) of reports.

Warning

H226 (93.3%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1971 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 4 件

Chemical: Octanal

Octanal is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octanal 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: 30-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5251

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

DOT LabelFlammable Liquid
Fire Hazards · 2 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire Potential · 2 件

Flammable liquid when exposed to heat, sparks, or flame

Moderate fire risk. Combustible.

Health Hazards · 2 件

Inhalation may be irritating to mucous membrane; overexposure may cause dizziness and collapse. Ingestion causes irritation of mouth and stomach. Contact with eyes or skin causes irritation. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 件

Category of C7-C9 aliphatic aldehydes and carboxylic acids: Members and supporting chemicals demonstrate low acute toxicity by oral, dermal, and inhalation exposures; toxicity in repeated-dose studies only at relatively high levels; no evidence of reproductive toxicity, developmental toxicity, or mutagenicity; [EPA ChAMP: Hazard Characterization] A skin, eye, and mucous membrane irritant; [CAMEO] A skin irritant; [eChemPortal: ERMA] An irritant; [MSDSonline]

安全と保護具

Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 件

Call for medical aid.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 3 件

Suitable extinguishing media: Dry powder, dry sand. Unsuitable extinguishing media: Do NOT use water jet.

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

To fight fire, use foam, carbon dioxide, 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. Storage class (TRGS 510): 3: Flammable liquids

毒性情報

Body BurdenFour of eight samples of human milk, from women living in Bayonne and Jersey City, New Jersey; Pittsburgh, PA; Baton Rouge, LA; Charleston, WV, contained octylaldehyde at unreported concentrations(1).
Interactions · 1 件

The effects of 16 aliphatic aldehydes with 3-10 carbons on the growth and patulin production of Penicillium expansum were examined. When P. expansum spores were inoculated into apple juice broth, some alkenals, including 2-propenal, (E)-2-butenal, (E)-2-pentenal, and (E)-2-hexenal, inhibited fungal growth and patulin production. Their minimal inhibitory concentrations were 5, 50, 80, and 80 ug/mL respectively. Vital staining indicated that these alkenals killed mycelia within 4 hr. Treatment of the spores with these aldehydes also resulted in rapid loss of germination ability, within 0.5-2 d. On the other hand, aliphatic aldehydes with 8-10 carbons significantly enhanced patulin production without affecting fungal growth: 300 ug/mL of octanal and 100 ug/mL of (E)-2-octenal increased the patulin concentrations in the culture broth by as much as 8.6- and 7.8-fold as compared to that of the control culture respectively. The expression of the genes involved in patulin biosynthesis in P. expansum was investigated in mycelia cultured in apple juice broth containing 300 ug/mL of octanal for 3.5, 5, and 7 d. Transcription of the msas gene, encoding 6-methylsalicylic acid synthase, which catalyzed the first step in the patulin biosynthetic pathway was remarkably high in the 3.5-d and 5-d-old cultures as compared with the control. However, octanal did not any increase the transcription of the msas in the 7-d-old culture or that of the other two genes, IDH and the peab1, in culture. Thus the enhanced patulin accumulation with supplementation with these aldehydes is attributable to the increased amount of the msas transcript.

Ecotoxicity Values · 3 件

LC50; Species: Alburnus alburnus (Bleak) wild caught; Conditions: saltwater, static; Concentration: 16 mg/L for 96 hr (95% confidence interval: 15-17 mg/L) /data for metabolic precursor, 1-octanol dissolved in water and acetone/

LC50; Species: Pimephales promelas (Fathead minnow) juvenile 26-34 days old; Conditions: freshwater, flow through; Concentration: 13.5 mg/L for 96 hr /data for metabolic precursor, 1-octanol/

LC50; Species: Nitocra spinipes (Harpacticoid) 3-6 wk old; Conditions: saltwater, static; Concentration: 58 mg/L for 96 hr (95% confidence interval: 53-64 mg/L) /data for metabolic precursor, 1-octanol dissolved in acetone/water/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a log Kow of 3.5(2) and a regression-derived equation(3), indicates that octylaldehyde is expected to have moderate mobility in soil(SRC). Volatilization of octylaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 5.14X10-4 atm-cu m/mole(4). Octylaldehyde has a vapor pressure of 0.6 mm Hg(2) and exists as a liquid under environmental conditions; therefore, octylaldehyde may volatilize from dry soil. Utilizing the Zahn-Wellens test, 77% degradation was reached using an activated sludge inoculum after 28 days(5) which indicates this compound is expected to biodegrade under certain environmental conditions in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a log Kow of 3.5(2) and a regression-derived equation(3), indicates that octylaldehyde may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a estimated Henry's Law constant of 5.14X10-4 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 5 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 60(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the Zahn-Wellens test, 77% degradation was reached using an activated sludge inoculum after 28 days(7) which indicates this compound is expected to biodegrade under certain environmental conditions in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octylaldehyde, which has a vapor pressure of 0.6 mm Hg at 20 °C(2), will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase octylaldehyde 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 12 hours(SRC), calculated from its rate constant of 3.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Octylaldehyde 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 · 4 件

Octylaldehyde has been reported in foods and beverages including, apple, apricot, many berries, guava, grapes, melon, papaya, celery, peas, potato, tomato, ginger, spearmint oil, hop oil, beer, rum, cider, white wine, cocoa, tea, roasted filberts and peanuts, pecans, oats, coconut products, soybean, avocado, passion fruit, starfruit, beans, mushroom, trassi, macadamia nut, sesame seed, mango, cauliflower, tamarind, loquat, angelica root oil and mastic gum oil(1).

Octylaldehyde was detected in peanut oil, heated to 200 °C, at unreported concentrations(1). Commercial rice cakes were found to contain 800-960 ppb of octylaldehyde(2). Octylaldehyde was identified in gari and farine, both products of cassava(3), in Beaufort cheese(4), roasted filberts(5), heated corn oil(6), kiwi fruit flowers(7), in both commercial and concentrated aqueous orange essences(8). Bisbee Delicious apples from Washington state emitted increasing concentrations of octylaldehyde through the end of August (to 1671.9 pL/kg-hr) but concentrations decreased in apples harvested after this point (to 32.4-141.9 pL/kg-hr)(9). Octylaldehyde was detected in raw and roasted earth almonds (Cyperus esculentus L.)(10). Octylaldehyde was detected in the emissions from heated rapeseed oil(11).Commercial samples of California navel orange, Florida Valencia orange, midseason orange, tangerine, and white grapefruit cold-pressed oils contained 0.161, 0.449, 0.358, 0.371, 0.493 wt% octylaldehyde, respectively(12). Octylaldehyde was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(13).

Octylaldehyde was identified as a volatile component of raw beef(1) and in scrambled eggs(2) at unreported concentrations. Octylaldehyde was measured at 999 ng/g and 1080 ng/g in big eyed herring paste and hair tail viscera paste, and was not detected in anchovy paste or shrimp paste(3). Octylaldehyde was detected in full fat and reduced fat frankfurters(4), Italian-type dry-cured ham(5), and as an odorant in cooked mussels (Mytilus edulis)(6). Octylaldehyde was released from charbroiling meat at 146,000 ug/kg of cooked meat(7). Aroma concentrates of uncured beef and chicken contained 0.69 mg/kg and 5.08 mg/kg octylaldehyde, respectively(8). Octylaldehyde was isolated as a volatile component of duck meat at 9.3 ppb, duck fat at 13.64 ppb, Cantonese style roasted duck at 9.66 ppb and Cantonese style roasted duck gravy at 38.08 ppb(9).

Octylaldehyde has been reported in cooked eggs and meats(1). Octylaldehyde has been detected in foal meat at increasing levels upon aging(2).

Milk Concentrations · 1 件

Octylaldehyde has been reported in cheeses, butter and milk(1). Four of eight samples of human milk, from women living in Bayonne and Jersey City, New Jersey; Pittsburgh, PA; Baton Rouge, LA; Charleston, WV, contained octylaldehyde at unreported concentrations(2).

法規制情報

FDA Requirements · 1 件

Octanal is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

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. Octanal is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

FIFRA Requirements · 3 件

Residues of 1-octanal 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: Odor masking agent. Limit: Not more than 0.2% of the pesticide formulation.

Residues of 1-octanal 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 animals. Use: Odor masking agent. Limit: Not more than 0.2% of the pesticide formulation.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. (a) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-contact surfaces in public eating places, dairy-processing equipment, and food-processing equipment and utensils. Octanal is included on this list. Limits: When ready for use, the end-use concentration is not to exceed 100 ppm.

安全データ

F
10
wgk
2
tsca
TSCA listed
rtecs
RG7780000
ridadr
UN 1191
毒性
LD50 orally in Rabbit: 4616 mg/kg LD50 dermal Rabbit 5207 mg/kg

化学と産業

薬理情報

Absorption, Distribution and Excretion · 1 件

Rats were nose exposed to an atmosphere containing 11.4 ppm of (11)C-octanal for 2 min. Inhaled octanal was absorbed from the lungs in a biphasic manner and the greatest concentration of octanal occurred in most tissues at 5 min. Tissue activities calculated on the basis of the administered dose and on the radiolabel retained until the animal was killed indicated a redistribution of the radiolabel as metabolic products after 20 min. The labeled carbon was eliminated in a biphasic manner as (11)CO2, which accounted for essentially all of the activity lost by the exposed rats.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

Found in rose and orange oils; Used in perfumes, flavors, and fragrances; Used to make linear alcohols; [HSDB]

For octylaldehyde (USEPA/OPP Pesticide Code: 128948) there are 0 labels match. /SRP: Not registered for current use in the USA, but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Perfumery, flavors.

Octanal is employed in the perfume industry for the preparation of synthetic citrus oils and for the synthesis of alpha-hexylcinnamaldehyde.

ingredient in some air fresheners

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

U.S. Production · 6 件

2023: 10,000,000 - <25,000,000 lb

(1975) 3.18X10+6 GRAMS

(1979) PROBABLY GREATER THAN 9.08X10+5 GRAMS

Octanal is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5197]

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

Consumer UsesFragrance
Industry UsesFragrance
Methods of Manufacturing · 2 件

By oxidation of the corresponding alcohol or reduction of the corresponding acid; also from coconut fatty acids via methyl-n-octoate.

Octanal can be obtained by hydroformylation of 1-heptene or by dehydrogenation of octanol.

Formulations/PreparationsGrade: Technical, FCC
応用分野 · 7 件

解説オクタナール (英: Octanal) とは、鎖状の有機化合物であり、アルデヒドの1種です。 化学式は、CH3(CH2)6CHOまたはC7H15CHOで表されます。モル質量は128.21204g/mol、密度は0.821g/ml、融点は-23℃、沸点は171℃、CAS登録番号は124-13-0です。 分岐鎖をもつ異性体と区別するために、直鎖のオクタナールをn-オクタナール (ノルマル-オクタナール) と表記することもあります。 別称は、オクタルデヒド、オクトアルデヒド、オクタンアルデヒド、オクチルアルデヒド、カプリルアルデヒド、1-オクタノンなどです。

用途石鹸、洗剤、香水、クリームの香り

説明May be prepared by oxidation of the corresponding alcohol or reduction of the corresponding acid; also from coconut fatty acids via methyl-n-octanoate.

天然物の起源Reported found in the essential oils of sweet orange, bitter orange, mandarin, tangerine, grapefruit, Mexican lime, lemon, Taiwan citronella, rose, lemongrass, Pinus sabiniana, Pinus jefferyi, Xanthoxylum rhetsa, lime petitgrain, clary sage, lavandin, and others. Also reported in over 180 foods and beverages including apple, apricot, many berries, guava, grapes, melon, papaya, celery, peas, potato, potato chips, tomato, ginger, spearmint oil, cheeses, butter, milk, cooked egg, fish and fish oil, meats, hop oil, beer, rum, cider, white wine, cocoa, tea, roasted filberts and peanuts, pecans, oats, coconut products, soybean, avocado, passion fruit, starfruit, beans, mushroom, trassi, macadamia nut, sesame seed, mango, cauliflower, tamarind, fig, calamus, rice, sweet potato, dill, lovage, caraway seed, corn oil, corn tortillas, loquat, shrimp, lobster, oyster, crab, crayfish, clam, maté, angelica root oil and mastic gum oil.

使用Octanal is an aromatic aldehyde often found in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry.

一般的な説明Colorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125°F. Used in making perfumes and flavorings.

使用用途1. 香料 オクタナールは、レモン油・オレンジ油などの香料の調合などが主な使用用途です。そのほかにも、ジャスミン・バラといった調合香料、塗料やワニスの原料としても使用用途があります。さらに、一部のアルコール飲料などに含まれている場合もあります。 また、アルデヒド基の部分がアセタール化された物質も独特のにおいをもっており、香料として市販されているように、オクタナールの誘導体も使用されていることが特徴です。 基本的には、本物質が有する独特の果実臭を利用した用途であるといえます。 2. 合成原料 オクタナールは比較長いアルキル鎖を持つアルデヒドであるため、さまざまな天然物の合成原料です。長鎖アルデヒドの構造を持つ天然物は海藻類などの生体内に含まれています。 特にオクタナールは、(−)-ジヒドロスポロトリオリド、(+)-テトラヒドロピレノホロール、および(+)-アワジャノマイシンの全合成に不可欠な前駆物質です。エリスリトールおよびペンタエリスリトールに基づくヒドロトロープの合成にも使用できます。

調製方法

製造方法By oxidation of the corresponding alcohol or reduction of the corresponding acid; also from coconut fatty acids via methyl-n-octoate.

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補足説明

定義ChEBI: A fatty aldehyde formally arising from reduction of the carboxy group of caprylic acid (octanoic acid).

関連反応

63 件

関連ノート

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