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Heptacosane

HCID 11636
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
593-49-7
Standard SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCC
InChIKey
BJQWYEJQWHSSCJ-UHFFFAOYSA-N
Molecular formula
C27H56
Average molar mass
380.7 g/mol
Monoisotopic mass
380.43820179

Overview

Heptacosane is a straight-chain alkane with 27 carbon atoms. It has a role as a volatile oil component and a plant metabolite.

Names & identifiers

Preferred name
Heptacosane
IUPAC
heptacosane
English name
N-Heptacosane
Molecular formula
C27H56
Molecular weight
380.73

Names & synonyms

HEPTACOSANEn-HeptacosaneEINECS 209-792-4AI3-36283DTXSID6058637CHEBI:32941HSDB 8357CH3-[CH2]25-CH3CH3-(CH2)25-CH3nHeptacosaneRefChem:145604DTXCID4032324
Show more names
Heptacosane>HEPTACOSANE 98+%N-HEPTACOSANE 95+%Farnesane Impurity 15C14122300 n-HeptacosaneHeptacosane >=98.0% (GC)
209-792-4BJQWYEJQWHSSCJ-UHFFFAOYSA-N593-49-7MFCD00009862VP371W2GJSUNII-VP371W2GJSn-HeptacosanALKANE C27

Database identifiers

CAS
593-49-7
PubChem CID
11636
DTXSID
DTXSID6058637
ChEBI
CHEBI:32941
UNII
VP371W2GJS
EC Number
209-792-4
Nikkaji
J452I

Properties

Computed structural properties

XLogP
14.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
24
Heavy atoms
27
Formal charge
0
Complexity
208

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Aliphatics, Saturated (>C11)

n-Alkane

LipidsFatty Acyls [FA] -> Hydrocarbons [FA11]
DensityDensity: 0.7796 g/cu cm at 60 °C
Color/FormCrystals form alcohol, benzene; leaves from ethyl acetate
Solubility · 2 items

Insoluble in water

Insoluble in ethanol; slightly soluble in ether

Boiling Point442 °C
Melting Point58.8 °C
Vapor Pressure · 2 items

VP: 1 Pa at 136.7 °C; 10 Pa at 168.8 °C; 100 Pa 206.5 °C; 1 kPa at 255.8 °C; 10 kPa at 323.3 °C; 100 kPa at 421.2 °C

2.8X10-9 mg/L at 25 °C (extrapolated)

Refractive IndexIndex of refraction: 1.4345 at 65 °C

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 · 3 items

This chemical does not meet GHS hazard criteria for 100% (5 of 5) of all reports.

Not Classified

Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Toxic Combustion ProductsCarbon oxides
Hazard Classes and CategoriesNot Classified
Skin, Eye, and Respiratory Irritations/Higher alkanes/ may cause eye and skin irritation.
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents

Safety & protection

Fire Fighting Procedures · 2 items

Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Non Combustible Solids
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: No special environmental precautions required. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

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 · 2 items

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/

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/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Physical Description
White crystalline powder; [Alfa Aesar MSDS]
Stability/Shelf LifeStable under recommended storage conditions.

Physicochemical properties

Melting point
58 · 58-60 °C(lit.)
Boiling point
270 °C15 · 270 °C15 mm Hg(lit.)
Density
0.7796 · 0.7796
refractive index
1.4345 · 1.4345
Flash point
270 °C/15mm · 270°C/15mm
storage temp.
Store at room temperature
Water Solubility
Insoluble in water
color
White to Almost white
BRN
1706242 · 1706242
Henry's Law Constant
7.7 · 7.7×10-9 mol/(m3Pa) at 25℃, Hilal et al. (2008)
InChI
1S/C27H56/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-27H2,1-2H3
InChIKey
BJQWYEJQWHSSCJ-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCCCCCCCCCCCCCCC
LogP
14.463 · 14.463 (est)
CAS DataBase Reference
593 · 593-49-7(CAS DataBase Reference)
FDA UNII
371 W2GJS · VP371W2GJS
EPA Substance Registry System
Heptacosane (593-49-7)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
RTECS
209 · 209-792-4
HS Code
29011000 · 29011000
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
593 · 593-49-7(Hazardous Substances Data)
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

Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.

ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: No special environmental precautions required.

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. Full contact

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

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.

Personal Protective Equipment (PPE) · 4 items

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. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

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

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.9X10+7(SRC), determined from a structure estimation method(2), indicates that heptacosane is expected to be immobile in soil(SRC). Volatilization of heptacosane from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 655 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Heptacosane is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 2.81X10-7 mm Hg at 25 °C(3). Biodegradation oxygen consumption values of 8.2 and 7.6 ug/mL for analogous tetracosane (C24) and hexatriacontane (C36), respectively, using a soil suspension(4) indicate that biodegradation of heptacosane may be a slow environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.9X10+7(SRC), determined from a structure estimation method(2), indicates that heptacosane 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 655 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 5.7 hours and 7.7 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 8(SRC), from an estimated log Kow of 13.60(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation oxygen consumption values of 8.2 and 7.6 ug/mL for analogous tetracosane (C24) and hexatriacontane (C36), respectively, using a soil suspension(6) indicate that biodegradation of heptacosane 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), heptacosane, which has an extrapolated vapor pressure of 2.81X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase heptacosane 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 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase heptacosane will be removed from the atmosphere by wet and dry deposition(SRC). Heptacosane 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: Heptacosane is a higher n-alkane containing 27 carbon atoms (C27). 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 liver, heart, kidneys, muscle and adipose bovine tissues.

Plant Concentrations · 2 items

Heptacosane detections in plants used in food and medicinal applications(1). /Heptacosane/[Table#8379]

n-Heptacosane detections in plants used in food and medicinal applications(1).

Animal Concentrations · 1 item

Heptacosane was found in several species of wasps, including Dolichovespula maculata and Vespula maculifrons; it was the major hydrocarbon at 14% in Vespula squamosa(1). The compound was found in the cuticular surface lipids of the cockroaches Leucophaea maderae and Blatta orientalis(2). Heptacosane was found in several species of fireflies including Lucidota atra, Photuris lucicrescens and Photuris cinctipennis(3).

Effluent Concentrations · 1 item

Alkanes (C20-C32) were the most abundant trace organic compounds found in particulate matter from vehicle exhaust with emission factors for heptacosane from diesel driven light-duty vehicles of 1.76-35.4 ug/km(1). Heptacosane was detected in the gas and particle phase of tailpipe emissions from non-catalyst equipped gasoline powered motor vehicles at concentrations of 2.4 and 391 ug/km, respectively(2).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of heptacosane can be estimated to be 3.9X10+7(SRC). According to a classification scheme(2), this estimated Koc value suggests that heptacosane is expected to be immobile in soil.

Natural Pollution Sources · 1 item

Heptacosane has been detected in various parts of a least 20 varieties of plants(1). Heptacosane was found in several species of wasps including Dolichovespula maculata, Vespula squamosa and Vespula maculifrons(2). Heptacosane was found in the cuticular surface lipids of the cockroaches: Leucophaea maderae and Blatta orientalis(3). Heptacosane was found in several species of fireflies including Lucidota atra, Photuris lucicrescens and Photuris Cinctipennis(4).

Atmospheric Concentrations · 3 items

URBAN/SUBURBAN: Heptacosane was detected in particulate air samples from Georgia Tech campus, GA at mean concentrations of 1.96 and 1.82 ng/cu m for summer 2005 and winter 2006, respectively(1). A mean heptacosane concentration of approximately 22 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). Heptacosane concentration was 11.9 and 8.5 ng/cu m in particulate phase in the summer and winter, respectively; the concentration was 3.1 and 1.0 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: Heptacosane was detected in particulate air samples from a rural area of Yorkville, GA at mean concentrations of 0.40 and 1.33 ng/cu m for summer and winter, respectively(1).

SOURCE DOMINATED: Heptacosane was detected at 140-1260 pg/cu m with a mean of 480 pg/cu m in particulate air samples collected near a highway in Raleigh, NC; concentrations in samples collected 275 meters from the highway contained 190-2000 pg/cu m with a mean of 490 pg/cu m(1). Heptacosane was detected in particulate air samples from an interstate highway in Georgia at a mean concentration of 2.69 and 2.56 ng/cu m for summer and winter, respectively(2).

Fish/Seafood ConcentrationsCatfish (Arius bilineatus) collected from seven locations in the Arabian Gulf had concentrations of C27 alkanes ranging from not detected to 2.9 ng/g wet weight(1).
Artificial Pollution SourcesAlkanes such as heptacosane 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 7.6 ug/mL over 10 days was reported for straight chain alkanes tetracosane (C24) and hexatriacontane (C36), 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 heptacosane (C27) 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. Data reported for similar long chain alkanes, hexacosane (C26), octacosane (C28), and triacontane (C30), which were present as components of the petroleum oil, indicate that these compounds were degraded by 4 of 5 bacterial strains with certain nitrogen sources, and consumption ranged from 5 to 96%(1).

Sediment/Soil ConcentrationsSEDIMENT: Heptacosane concentrations were 7.7-429 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).

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
209-792-4
hs_code
29011000
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazardous Substances Data
593-49-7(Hazardous Substances Data)
General Manufacturing Information · 1 item

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/

Applications

UsesRefer to the productμs Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Preparation methods · 1 item

PreparationWeigh 11.4 g of 10,18-heptadecanedione, 25 mL of hydrazine monohydrate, 25 mL of glacial acetic acid, and 305 mL of 1-octanol, and reflux at 140-150 °C for 9 hours with stirring. Remove the water and excess hydrazine formed using a Dean-Stark apparatus. Add a sodium octanoate solution (11 g sodium dissolved in 120 mL of 1-octanol) to the hydrazone. Then reflux the mixture for 24 hours. Raise the oil bath temperature to 180 °C. Neutralize the cold mixture with 4 M HCl. Evaporate the organic phase to dryness under vacuum (~133 Pa). The remaining semi-solid was crystallized from ethanol to give an impure white solid, which was finally purified by silica gel column chromatography (eluent toluene) to give N-HEPTACOSANE in 29% yield, with a melting point of 59 °C.

Additional notes

DefinitionChEBI: A straight-chain alkane with 27 carbon atoms.