1-Heptanol is an alcohol with a seven carbon chain and the structural formula of CH3(CH2)6OH.It is a clear colorless liquid that is very slightly soluble in water, but miscible with ether and ethanol.
There are three other isomers of heptanol that have a straight chain, 2-heptanol, 3-heptanol, and 4-heptanol, which differ by the location of the alcohol functional group.
Heptanol is commonly used in cardiac electrophysiology experiments to block gap junctions and increase axial resistance between myocytes. Increasing axial resistance will decrease conduction velocity and increase the heart's susceptibility to reentrant excitation and sustained arrhythmias.
1-Heptanol, also known as heptan-1-ol or heptyl alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 1-heptanol is considered to be a fatty alcohol lipid molecule. 1-Heptanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
1-heptanol is an alkyl alcohol that is heptane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Capillipedium parviflorum. It has a role as a plant metabolite, a fragrance and a flavouring agent. It is a primary alcohol, an alkyl alcohol and a volatile organic compound. It derives from a hydride of a heptane.
1-Heptanol is primarily oxidized in the rabbit to heptanoic acid, which either undergoes further oxidation to CO2 or forms an ester glucuronide. There is also a lesser metabolic pathway using direct conjugation with glucuronic acid to form an ether glucuronide conjugate.
The epicardial surface of 12 isolated-perfused canine left atria was optically mapped before and after 1-50 microM heptanol infusion. At baseline, no sustained (>30 s) AF could be induced in any of the 12 tissues. However, after 2 microM heptanol infusion, sustained AF was induced in 9 of 12 tissues (P < 0.001). Heptanol >5 microM caused loss of 1:1 capture during rapid pacing, causing no AF to be induced. ... Heptanol at 2 microM had no effect on the cellular action potential duration restitution or on the maximal velocity rate over time of the upstroke. The effects of heptanol were reversible.
The experiments investigated the effects of heptanol on isolated Langendorff-perfused rabbit hearts. Heptanol inhibited both pressure generation and electrical conduction. These effects were completely reversible ... Low concentrations of heptanol (less than 0.3 mM) caused small but significant increases in the delay between the stimulus (delivered to the basal septum) artifact and local activation of the left ventricle, as measured from bipolar electrogram (BEG) recordings. There was a steep increase in the latency between stimulus and left-ventricular activation at concentrations of heptanol above 0.3 mM ... Heptanol decreased repolarization duration, measured from the activation recovery interval (ARI) of BEGs, and monophasic action potential duration at 70% repolarization (MAPD70). Heptanol also reduced left-ventricular developed pressure (LVDP), and the maximum rates of contraction and relaxation of the left ventricle; these effects were concentration dependent and reversible. Changes in ARIs, LVDP and the maximum rates of change of pressure lacked the steep response to 0.3 to 1.0 mM heptanol shown by the latency ... During premature stimulation protocols arrhythmias could be induced in hearts perfused with 0.1 to 0.3 mM heptanol but not at higher concentrations.
Incubation of n-heptane with microsomal extracts resulted in formation of four isomeric n-heptanols. The relationship of the hydroxylating process to protein concentration and to the formation of the three main alcoholic products, namely 1-heptanol (111706), 2-heptanol (543497), and 3-heptanol (589822), were linear up to 1mg/4 minutes. Treatment of rats with phenobarbitol (50066) for 2 days enhanced hydroxylation and formation of 2-heptanol, 3-heptanol and 4-heptanol about 4 fold, but 1-heptanol was increased only 60 percent. In contrast, 3,4-benzpyrene depressed the formation of 1-heptanol to about 70 percent and increased the formation of 3-heptanol and 4-heptanol slightly. Carbon-monoxide inhibited formation of 1-heptanol. Similar results were obtained with metyrapone.
Heptanol caused a significant growth inhibition of Xenopus tadpoles and the median lethal dose and mean teratogenic effect at 120 hours were 1.49 and 0.37 millimolar, respectively. The teratogenic index of 4.03 suggested that heptanol is a strong teratogen.
In the United States, practically the whole production is processed further to phthalates or adipates, used as plasticizers. ... The alcohol mixtures are used as solvents or solubilizers in the paint and printing ink sector, as components in textile auxiliaries and pesticides, for hormone extraction, and in the surfactant field as foam boosters or antifrothing agents.
Prepared from heptaldehyde by reduction with iron filings in dilute acetic acid. ... Other methods include reaction between pentane and ethylene oxide in presence of anhydrous aluminum bromide: I.G. Farbenind., French patent 716,604 ... and action of amyl magnesium bromide on ethylene oxide.
By reduction of enanthic aldehyde, which is a distillation product of castor oil.
From 1-hexene by oxo synthesis.
1-Heptanol is made by the oxo process by reacting hexenes with carbon monoxide .
Commercial products from the family of 6 to 11 carbon alcohols that make up the plasticizer range are available both as ... pure single carbon chain materials and as complex isomeric mixtures. Commercial descriptions of plasticizer range alcohols are ... in general a ... pure material is called "-anol" /eg, 1-heptanol/, and the mixtures are called "-yl alcohol /eg, heptyl alcohol/ or "iso ... yl alcohol" /eg, isoheptyl alcohol/.
CHROMATOGRAPHIC DETERMINATION OF COMPOSITION OF LOWER ALIPHATIC ALCOHOLS IN WASTE WATER. SENSITIVITY OF DETECTION WAS 10-6% USING A FLAME IONIZATION DETECTOR.
AEROBIC: 1-Heptanol degrades fast in aerobic biodegradation screening tests(1-5). In a 5-day BOD test using acclimated mixed cultures, 56.3% of theoretical BOD was consumed(1). Other tests show 30% of theoretical BOD was expended in 5 days(2) and 28.9% of theoretical BOD was expended in 1 day using 500 ppm of 1-heptanol and an activated sludge inoculum(3). An aerobic biodegradation rate constant of 0.124 1/hr(4), which corresponds to a half-life of 0.23 days(SRC), was determined in an aerobic screening test at pH 7 and 25 °C using an activated sludge inocula. In a similar screening test, the rate constant was measured to be 2.53X10-2 1/hr(5), which corresponds to a biodegradation half-life of 1.14 days(SRC).
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS.
HEPTANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Heptyl alcohol 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: 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, and 2) 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.
Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/
Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/
1-Heptanol's production and use as an intermediate, primarily in the production of plasticizers, and as a solvent and solubilizing agent may result in its release to the environment through various waste streams. It is also a natural product found in plants, meats, fruits, vegetables and even in the expired air of healthy, unexposed people. If released to air, a vapor pressure of 0.216 mm Hg at 25 °C indicates 1-heptanol will exist solely as a vapor in the atmosphere. Vapor-phase 1-heptanol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 28 hours. If released to soil, 1-heptanol is expected to have high mobility based upon an estimated Koc of 74. Volatilization from moist soil surfaces is expected to be an important fate process based upon a Henry's Law constant of 1.88X10-5 atm-cu m/mole. 1-Heptanol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data show theoretical 5 day BODs of 30% and 56.3% and 1 day theoretical BOD of 28.9%. If released into water, 1-heptanol is not expected to adsorb to suspended solids and sediment based upon the Koc. Biodegradation half-lives of 0.2 days and 1.14 days where observed using activated sludge inoculum. Volatilization from water surfaces is expected to be an important fate process based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 2.2 days and 20 days, respectively. An estimated BCF of 21 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 1-heptanol may occur through inhalation and dermal contact with this compound at workplaces where 1-heptanol is produced or used. Monitoring data indicate that the general population may be exposed to 1-heptanol via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing 1-heptanol.
1-Heptanol is a volatile chemical found in plants(1), essential oils, such as hyacinth, violet leaves, and Litsea zeylanica(2), meats(3,4), fruits(5,6) and vegetables(7,8). 1-Heptanol has been identified in the emissions from Dawn redwood trees(9).
1-Heptanol's production and use as an intermediate in the manufacture of plasticizers (phthalates and adipates) and as solvents or solubilizers in the paint and printing ink industry and other sectors(1) may result in its release to the environment through various waste streams. Pure 1-heptanol is not used for these purposes but rather isomeric mixtures of C7 alcohols and C7-C11 alcohol mixtures(1).
Watery colorless liquid with a weak alcohol odor. Floats on water.
COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.
FAINT, AROMATIC, FATTY
PUNGENT, SPICY TASTE
Water solutions are colloidal
BP: 155.6 °C at 400 mm Hg; 136.6 °C at 200 mm Hg; 119.5 °C at 100 mm Hg; ... 85.8 °C at 20 mm Hg; 74.7 °C at 10 mm Hg; 64.3 °C at 5 mm Hg; 42.4deg C at 1.0 mm Hg
Henry's Law constant = 1.88X10-5 atm-cu m/mol at 25 °C
Hydroxyl radical reaction rate constant = 1.37X10-11 cu cm/molec-sec at 25 °C
Physical State Liquid
Odor Threshold No data available
Melting Point/Range -35 °C / -31 °F
Softening Point No data available
Boiling Point/Range 176 °C / 348.8 °F @ 760 mmHg
Flammability (liquid) Combustible liquid On basis of test data
Flammability (solid,gas) Not applicable Liquid
Explosion Limits No data available
Flash Point 73 °C / 163.4 °F Method - No information available
Autoignition Temperature 350 - °C / 662 - °F
Decomposition Temperature No data available
pH No information available
Viscosity No data available
Water Solubility Insoluble in cold water
Solubility in other solvents No information available
Molecular Formula C7 H16 O
Molecular Weight 116.2
Explosive Properties explosive air/vapour mixtures possible
CAS number 111-70-6
Weight Average: 116.2013
InChI Key BBMCTIGTTCKYKF-UHFFFAOYSA-N
IUPAC Name heptan-1-ol
Traditional IUPAC Name heptanol
Chemical Formula C7H16O
Description belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
Kingdom Organic compounds
Super Class Lipids and lipid-like molecules
Class Fatty Acyls
Sub Class Fatty alcohols
Direct Parent Fatty alcohols
Organic oxygen compound
Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
Other names: Heptyl alcohol n-Heptan-1-ol n-Heptanol n-Heptyl alcohol Enanthic alcohol Gentanol 1-Hydroxyheptane n-C7H15OH Heptan-1-ol Heptane-1-ol Heptyl alcohol, n- n-Heptanol-1 l’Alcool n-heptylique primaire Alcohol C7 Enanthyl alcohol 1-Heptyl alcohol Heptanol-1 NSC 3703 Formula: C7H16O CAS: 111-70-6 Weight: 116,2013 g/mol Boiling point: 176 °C Melting point: -36 °C Density: 0,822 g/cm3
C7H15OH An alcohol; a fragrant, colorless liquid boiling at 174°C; soluble in water, ether, or alcohol; used as a chemical intermediate, as a solvent, and in cosmetics. Also known as heptyl alcohol.
Synonyms: ALCOHOL C-7, ENANTHIC ALCOHOL
Chemical Names: 1-HEPTANOL
JECFA number: 94
COE number: 70
FEMA number: 2548
Evaluation year: 1997
ADI: No safety concern at current levels of intake when used as a flavouring agent
Specs Code: N
Report: TRS 884-JECFA 49/29
Tox Monograph: FAS 40-JECFA 49/147
Specification: COMPENDIUM ADDENDUM 5/FNP 52 Add.5/214
Molecular weight: 116.2013
IUPAC Standard InChI:
Download the identifier in a file.
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IUPAC Standard InChIKey: BBMCTIGTTCKYKF-UHFFFAOYSA-N
CAS Registry Number: 111-70-6
Chemical structure: C7H16O
This structure is also available as a 2d Mol file or as a computed 3d SD file
Species with the same structure:
Other names: Heptyl alcohol; n-Heptan-1-ol; n-Heptanol; n-Heptyl alcohol; Enanthic alcohol; Gentanol; 1-Hydroxyheptane; n-C7H15OH; Heptan-1-ol; Heptane-1-ol; Heptyl alcohol, n-; n-Heptanol-1; l'Alcool n-heptylique primaire; Alcohol C7; Enanthyl alcohol; 1-Heptyl alcohol; Heptanol-1; NSC 3703; 1-HeptanoI
Information on this page:
Gas phase thermochemistry data
Other data available:
Condensed phase thermochemistry data
Phase change data
Reaction thermochemistry data
Henry's Law data
Gas phase ion energetics data
Mass spectrum (electron ionization)
Flavouring Heptyl alcohol
Synonym(s) Enanthic alcohol;Alcohol C-7
Latest JECFA evaluation 1997 (Session 49)
Status of specification Full
Chemical name 1-Heptanol
JECFA number 94
CAS number 111-70-6
FEMA number 2548
COE number 70
FLAVIS number -
Molecular weight 116.2
Chemical formula C7H16O
Physical form/odour colourless liquid/citrus odour
Solubility slightly soluble in water; miscible with alcohol, ether, most fixed oils
Solubility in ethanol 1 ml in 2 ml 60% alcohol
Boiling point (°C) 175°
Assay min % 97.0%
Acid value max 1
Refractive index 1.423-1.427
Specific gravity 0.820-1.824
Other requirements Aldehydes: 1.0% as heptanal
l'Alcool n-heptylique primaire
HEPTYL ALCOHOL, N-
Heptyl alcohol, primary
FEMA Number 2548
Heptyl alcohol (natural)
FEMA No. 2548
l'Alcool N-heptylique primaire [French]
Heptyl alcohol, 8CI
4-01-00-01731 (Beilstein Handbook Reference)
Heptyl alcohol, natural, 98%
1-Heptanol, analytical standard