Octanal

HCID 454CAS 124-13-0

Basic information

Standard SMILES
CCCCCCCC=O
InChIKey
NUJGJRNETVAIRJ-UHFFFAOYSA-N
Molecular formula
C8H16O
Average molar mass
128.21 g/mol
Monoisotopic mass
128.12011513

Overview

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.

Names & identifiers

Preferred name
Octanal
IUPAC
octanal
English name
Octanal
Molecular formula
C8H16O
Molecular weight
128.21

Names & synonyms

Octanal124-13-0CaprylaldehydeCaprylic aldehyden-Octanal1-octanaln-Octyl aldehyden-Caprylaldehyden-OctaldehydeOctanaldehyden-OctylalAldehyde C-8
Show more names
OCTYL ALDEHYDEFEMA 2797ORANGE ALDEHYDENatural Doctanal
Octanoic aldehydeOctaldehydeC-8 aldehydeOCTYLALDEHYDE1-Octylaldehyde1-Octaldehyde1-CaprylaldehydeOctanal, tech.

Database identifiers

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

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
9

Experimental & physicochemical properties

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

log Kow = 3.5 at pH 6.9 (by HPLC)

2.53

Odor · 3 items

Strong, fruity odor

Fatty, citrus, honey odor on dilution

Pungent odor; citrus-like on dilution

Physicochemical properties

Melting point
12 · 12-15 °C(lit.)
Boiling point
171 °C · 171 °C(lit.)
Density
0.822 g/mL · 0.822 g/mL at 20 °C
vapor pressure
2 mm · 2 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.421(lit.)
FEMA
2797 · 2797 | OCTANAL

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 4 items

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 items

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

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

Fire Potential · 2 items

Flammable liquid when exposed to heat, sparks, or flame

Moderate fire risk. Combustible.

Health Hazards · 2 items

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 item

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]

Safety & protection

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

· 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 items

Call for medical aid.

General First Aid:

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

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

Toxicology

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 item

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 items

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 items

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 items

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 item

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).

Regulatory information

FDA Requirements · 1 item

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 items

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 items

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.

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
RG7780000
ridadr
UN 1191

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

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

Uses & manufacturing

Uses · 6 items

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 items

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 items

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
Applications · 4 items

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

OccurrenceReported 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.

UsesOctanal 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.

General DescriptionColorless liquids with a strong fruity odor. Less dense than water and insoluble in water. Flash points 125°F. Used in making perfumes and flavorings.

Preparation methods

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

Suppliers5 total

厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
湖北拓源精细化工有限公司027-84700466 13260688474 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]

Additional notes

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

Related reactions

63 records

Linked notes

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