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Hexacosane

HCID 12407
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Basic information

CAS
630-01-3
Standard SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCC
InChIKey
HMSWAIKSFDFLKN-UHFFFAOYSA-N
Molecular formula
C26H54
Average molar mass
366.7 g/mol
Monoisotopic mass
366.42255172

Overview

N-hexacosane appears as colorless crystals. Occurs in many natural products.

Names & identifiers

Preferred name
Hexacosane
IUPAC
hexacosane
English name
n-Hexacosane
Molecular formula
C26H54
Molecular weight
0

Names & synonyms

HEXACOSANEn-HexacosaneCH3-[CH2]24-CH3HEXACOSANE, N-EINECS 211-124-1UNII-0CI4OKE9VONSC-122457DTXSID7060883CHEBI:32940HSDB 8356CH3-(CH2)24-CH3nHexacosane
Show more names
Hexacosane, nRefChem:145915DTXCID3043601211-124-1HMSWAIKSFDFLKN-UHFFFAOYSA-N630-01-3MFCD000093540CI4OKE9VO

Database identifiers

CAS
630-01-3
PubChem CID
12407
DTXSID
DTXSID7060883
ChEBI
CHEBI:32940
UNII
0CI4OKE9VO
EC Number
211-124-1
Nikkaji
J527D

Properties

Computed structural properties

XLogP
13.7
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
23
Heavy atoms
26
Formal charge
0
Complexity
196

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Aliphatics, Saturated (>C11)

n-Alkane

LipidsFatty Acyls [FA] -> Hydrocarbons [FA11]
Density · 2 items

0.8032 at 68 °F (NTP, 1992) - Less dense than water; will float

Density: 0.7783 g/cu cm at 60 °C

Color/FormMonoclinic, triclinic or orthorhombic crystals from benzene; crystals from ether
SolubilityVery soluble in benzene, ligroin, chloroform
Boiling Point · 2 items

774 °F at 760 mmHg (NTP, 1992)

415 °C

Melting Point · 2 items

133.5 °F (NTP, 1992)

56.09 °C

Vapor Pressure · 2 items

VP: 1 Pa at 125.1 °C; 10 Pa at 158.8 °C; 100 Pa 200.1 °C; 1 kPa at 252.1 °C; 10 kPa at 314.3 °C; 100 kPa at 411.3 °C

4.69X10-07 mm Hg at 25 °C (extrapolated)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (5 of 10) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P280, P302+P352, P321, P332+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 10 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationHexacosane: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data on this compound is not available, but it is probably combustible. (NTP, 1992)
Hazards SummaryA skin irritant; [Alfa Aesar MSDS]
Reactive GroupHydrocarbons, Aliphatic Saturated
Reactivity Profile · 1 item

Saturated aliphatic hydrocarbons, such as N-HEXACOSANE, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, they burn exothermically to produce carbon dioxide and water.

Air and Water ReactionsInsoluble in water.
Toxic Combustion Products

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

Liver, heart, kidneys, muscle and adipose (perirenal and s.c.) /bovine/ tissues were collected from 6 animals for analysis of their hydrocarbon composition. Qualitative and quantitative determinations were carried out by gas chromatography and combined gas chromatography-mass spectrometry. Although differing in the proportions, a homologous series of n-alkanes ranging from n-C12-n-C31 was found in all samples. The isoprenoid hydrocarbons phytane and phytene (phyt-1-ene and phyt-2-ene) were also identified. (These findings have relevance to the health of humans consuming hydrocarbon-contaminated meats.) /n-Alkanes/

Uses & manufacturing

Uses · 4 items

Found in many natural products; [CAMEO]

For n-hexacosane (USEPA/OPP Pesticide Code: 400004) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

They are used mainly in applications for which isoalkanes are not acceptable for biological reasons, e.g., the production of detergents or proteins. /Higher n-Alkanes/

Solid n-alkanes (paraffin waxes) are used in a variety of applications, e.g., ... oxidation, and chlorination reactions. /Higher n-Alkanes/

Methods of Manufacturing · 2 items

The liquefaction of coal provides the greatest variety of saturated hydrocarbons. The Fischer-Tropsch synthesis produces alkanes from syngas (CO + H2) in the range C1 to C30 or higher depending on the process variant: depending on the catalyst employed, the synthesis yields predominantly liquid hydrocarbons in the gasoline range, along with gases from C1 to C4 when iron-based catalysts are used, while cobalt-based catalysts produce longer chain hydrocarbons in the diesel and wax range that often undergo, depending of the desired product slate, further processing, especially for gasoline generation. While iron-based Fischer-Tropsch catalysts generate complex mixtures that also include branched and olefinic hydrocarbons, cobalt-based catalysts produce streams that are rich in n-alkanes and are therefore suitable raw materials for detergents and for wax products. /Saturated Hydrocarbons/

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Refractive Index
Index of refraction: 1.4357 at 60 °C
Physical Description · 2 items

N-hexacosane appears as colorless crystals. Occurs in many natural products.

Colorless solid; [CAMEO] White odorless crystals; [Alfa Aesar MSDS]

Stability/Shelf LifeStable under recommended storage conditions.

Physicochemical properties

Melting point
56.4 °C · 56.4 °C
Boiling point
412.2 °C · 412.2 °C
Density
0.778 g/cm3 · 0.7780 g/cm3(Temp: 70 °C)
Special hazards arising from the substance or mixture: Carbon oxides.
Skin, Eye, and Respiratory Irritations/Higher alkanes/ may cause eye and skin irritation.
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.

Safety & protection

Fire FightingTo extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Fire Fighting Procedures · 2 items

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

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

Nonfire Spill ResponseSMALL SPILLS AND LEAKAGE: 1.
Disposal Methods · 2 items

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Preventive Measures · 5 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

Appropriate engineering controls: General industrial hygiene practice.

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.

For more Preventive Measures (Complete) data for n-Hexacosane (6 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 5 items

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.

Eye/face protection: 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: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Toxicology

Environmental Fate · 3 items

TERRESRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.1X10+7(SRC), determined from a structure estimation method(2), indicates that hexacosane is expected to be immobile in soil(SRC). Volatilization of hexacosane from moist soil surfaces is expected to be a fate process(SRC) given an estimated Henry's Law constant of 490 atm-cu m/mole(SRC), using a fragment constant estimation method(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Hexacosane is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 4.69X10-07 mm Hg at 25 °C(3). Biodegradation oxygen consumption values of 8.2 and 7.8 ug/mL for analogous tetracosane (C24) and dotriacontane (C32), respectively, using a soil suspension(4) indicate that biodegradation of hexacosane may be a slow environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.1X10+7(SRC), determined from a structure estimation method(2), indicates that hexacosane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 490 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.6 hours and 7.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is more than 2 years if adsorption is considered (4). According to a classification scheme(5), an estimated BCF of 13.5(SRC), from an estimated log Kow of 13.1(2), suggests the potential for bioconcentration in aquatic organisms is low (SRC). Biodegradation oxygen consumption values of 8.2 and 7.8 ug/mL for analogous tetracosane (C24) and dotriacontane (C32), respectively, using a soil suspension(6) indicate that biodegradation of hexacosane may be a slow environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexacosane, which has an extrapolated vapor pressure of 4.69X10-07 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hexacosane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.1 hours (SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hexacosane will be removed from the atmosphere by wet and dry deposition(SRC). Hexacosane 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).

Toxicity Summary · 1 item

IDENTIFICATION AND USE: Hexacosane is a solid n-alkane containing 26 carbon atoms (C26). Solid n-alkanes (paraffin waxes) are used in a variety of applications: as feeds for cracking them to gasoline blendstock materials, oxidation, and chlorination reactions. HUMAN EXPOSURE AND TOXICITY: There are no data available. ANIMAL STUDIES: A homologous series of n-alkanes ranging from n-C12-n-C31 was found in all samples of bovine tissues.

Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ Embryonic inland silversides, Meinida beryllina, were exposed to neutral, water-soluble fractions (WSFs) resulting from microbial degradation of artificially weathered Alaska North Slope (ANS) crude oil. Three individual microbes obtained from Prince William Sound, Alaska, and designated Phe#6 (enriched on phenanthrene), Hexaco#2 (enriched on the straight-chain alkane, hexacosane), and EI2V (grown by enrichment on Bushnell-Haas medium containing 0.2% pristane, a branched alkane) were used to individually biodegrade weathered ANS crude oil for 14 days in darkness in 20-L glass carboys containing nutrient enriched, sterilized 20% salinity sea water at 20 +/- 1 degrees C. Neutral WSFs resulting from biodegradation of ANS (lot 521) by each microbe were recovered and weighted. Neutral WSFs recovered were: 1.76 mg/L for Phe#6, 1.85 mg/L for Hexaco#2, and 13.02 mg/L for the EI2V microbe. Embryo toxicity and teratogenicity tests revealed that exposure of embryos to the WSFs from the EI2V incubation (with a total recovered neutral fraction approximately seven times greater than the Phe#6 and Hexaco#2 incubations) resulted in the most severe responses in craniofacial, cardiovascular, and skeletal organ systems. The total neutral WSFs recovered from the EI2V biodegradation of weathered ANS 521 were subfractionated into saturated (eluted with hexane), aromatic (eluted with CH2Cl2), polar (eluted with ethyl ether), and recombined (saturated + aromatic + polar) fractions. Developing fish embryos were then exposed to each subfraction and the recombined subfractions. The polar subfraction and recombined subfractions proved to be the most embryo toxic and teratogenic. They resulted in statistically significant (p < or = 0.05) responses (compared to controls) for craniofacial, cardiovascular, skeletal, and total severity effects in one or both tests with these subfractions.

Plant Concentrations · 2 items

Hexacosane detections in plants used in food and medicinal applications(1). /Hexacosane/[Table#8377]

n-Hexacosane detections in plants used in food and medicinal applications(1).[Table#8378]

Effluent ConcentrationsAlkanes (C20-C32) were the most abundant trace organic compounds found in particulate matter from vehicle exhaust with emission factors for hexacosane from diesel driven light-duty vehicles of 3.42-78.2 ug/km(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of hexacosane can be estimated to be 2.1X10+7 (SRC). According to a classification scheme(2), this estimated Koc value suggests that hexacosane is expected to be immobile in soil.

Natural Pollution SourcesHexacosane has been detected in various parts of a least 15 varieties of plants(1).
Atmospheric Concentrations · 3 items

URBAN/SUBURBAN: Hexacosane was detected in particulate air samples from Georgia Tech campus, GA at mean concentrations of 1.15 and 2.33 ng/cu m for summer 2005 and winter 2006, respectively(1). A mean hexacosane concentration of approximately 18 ng/cu m was reported in the particulate phase of air samples collected in an urban and industrialized area in Prato, Italy during 2002(2). Hexacosane concentration was 8.2 and 8.7 ng/cu m in particulate phase in the summer and winter, respectively; the concentration was 5.6 and 0.9 ng/cu m in the vapor phase in summer and winter, respectively; samples were collected in an urban area in Nagoya, Japan in 1991(3).

RURAL/REMOTE: Hexacosane was detected in particulate air samples from a rural area of Yorkville, GA at mean concentrations of 0.29 and 1.74 ng/cu m for summer and winter, respectively(1).

SOURCE DOMINATED: Hexacosane was detected in the gas and particle phase of tailpipe emissions from non-catalyst equipped gasoline powered motor vehicles at concentrations of 9.6 and 764 ug/km, respectively(1). Hexacosane was detected at 61-650 pg/cu m with a mean of 220 pg/cu m in particulate air samples collected near a highway in Raleigh, NC; concentrations in samples collected 275 meters from the highway contained 70-740 pg/cu m with a mean of 190 pg/cu m(2). Hexacosane was detected in particulate air samples from an interstate highway in Georgia at a mean concentration of 1.93 and 4.00 ng/cu m for summer and winter, respectively(3).

Artificial Pollution SourcesAlkanes such as hexacosane may be components in petroleum products(1) and may be released to the environment through the processing and combustion of petroleum products(SRC).
Environmental Biodegradation · 2 items

AEROBIC: Oxygen consumption of 8.2 and 7.8 ug/mL over 10 days was reported for straight chain alkanes tetracosane (C24) and dotriacontane (C32), respectively, using a soil suspension of Hudson-Collamer silt loam soil incubated in the dark at 25 °C(1). By analogy, these test results suggest that biodegradation rates are slow for long chain alkanes such as hexacosane (C26) under these conditions(SRC).

PURE CULTURE: Using 5 different marine bacterial strains and 4 different nitrogen sources, biodegradation of petroleum oil was examined under aerobic conditions at 26 °C for 10 days; hexacosane, present as a component of the petroleum oil, was degraded by 4 of 5 bacterial strains with certain nitrogen sources, consumption ranged from 10 to 91%(1). Biodegradation of hexacosane has occurred in the presence of two petroleum sludge bacteria, Pseudomonas sp. and Stenotrophomonas nitritireducens. Both strains metabolized hexacosane by 82%. When combined, 98% metabolism was observed. However, abiotic degradation accounted for 21% metabolism(2).

Sediment/Soil ConcentrationsSEDIMENT: Hexacosane concentrations were 0.7-133 ng/g dry weight in sediments samples collected from 14 sites from the Shinano River in Niigata, Japan from November 2005 to April 2006(1).
Environmental Bioconcentration · 1 item

An estimated BCF of 13.5 was calculated in fish for hexacosane(SRC), using an estimated log Kow of 13.1(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not metabolized by the organism(SRC).

Suitable sources for n-alkanes with more than six carbon atoms are the appropriate petroleum distillate fractions, from which the n-paraffins can be isolated in high isomeric purity (= 95% linearity) by selective separation techniques, especially fractional distillation. /Higher n-Alkanes/

General Manufacturing Information · 2 items

Hexacosane: ACTIVE

Gas-phase dehydrogenation of n-alkanes over noble-metal catalysts yield the corresponding n-alkenes at low conversion rates (ca. 10%) with predominantly internal double bonds. The corresponding alkenes can be isolated in high purity by selective molecular-sieve processes. /Higher n-Alkanes/

Additional notes

DefinitionChEBI: Hexacosane is a straight-chain alkane comprising of 26 carbon atoms. It has a role as a volatile oil component and a plant metabolite.