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2-heptanol

Chemical Structure

General Material Information

Preferred name 2-heptanol
Trivial Name 2-Heptanol
Short Description amyl methyl carbinol
Formula C7 H16 O
CAS Number 543-49-7
Deleted CAS Number 52390-72-4
FEMA Number 3288
Flavis Number 2.045
ECHA Number 208-844-3
FDA UNII E12FIG07JK
Nikkaji Number J6.402E
Beilstein Number 1719088
MDL MFCD00004587
COE Number 554
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 284 2-heptanol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 543-49-7 ; 2-HEPTANOL
Synonyms
  • amyl methyl carbinol
  • N- amyl methyl carbinol
  • heptan-2-ol
  • 2 heptanol
  • 2-heptanol natural
  • 2-heptyl alcohol
  • sec- heptyl alcohol
  • heptyl alcohol, sec-
  • 2-hydroxyheptane
  • methyl amyl carbinol
  • methyl N-pentyl carbinol
  • methyl pentyl carbinol
  • methylhexanol
  • 1-methylhexanol
  • s-Heptyl alcohol
  • 2-Hydroxyheptane
  • 2-Heptyl alcohol
  • 1-Methylhexanol
  • (±)-2-Heptanol
  • DL-Heptan-2-ol
  • NSC 2220
  • 1-Methyl-1-hexanol

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
heptan-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:543-49-7
Pubchem (cid):10976
Pubchem (sid):134976517
Flavornet:543-49-7
Pherobase:View
Publications by PubMed
Contrasting Effects of Ethylene Biosynthesis on Induced Plant Resistance against a Chewing and a Piercing-Sucking Herbivore in Rice.
Cofactor Specificity Engineering of Streptococcus mutans NADH Oxidase 2 for NAD(P)(+) Regeneration in Biocatalytic Oxidations.
Volatile and amino acid profiling of dry cured hams from different swine breeds and processing methods.
Influence of the stereochemistry on the sensory properties of 4-mercapto-2-heptanol and its acetyl-derivatives.
Formation of the aroma of a raw goat milk cheese during maturation analysed by SPME-GC-MS.
New cysteine-S-conjugate precursors of volatile sulfur compounds in bell peppers (Capsicum annuum L. cultivar).
Fragrance material review on 2,6-dimethyl-2-heptanol.
Preparation of passion fruit-typical 2-alkyl ester enantiomers via lipase-catalyzed kinetic resolution.
Influence of pre-cure freezing on the profile of volatile compounds during the processing of Iberian hams.
Stingless bees: chemical differences and potential functions in Nannotrigona testaceicornis and Plebeia droryana males and workers.
Comparison of chemical compositions and antimicrobial activities of essential oils from three conifer trees; Pinus densiflora, Cryptomeria japonica, and Chamaecyparis obtusa.
Comparative analysis of chemical compositions and antimicrobial activities of essential oils from Abies holophylla and Abies koreana activities of essential oils from Abies holophylla and Abies koreana.
Repellent activity of alligator pepper, Aframomum melegueta, and ginger, Zingiber officinale, against the maize weevil, Sitophilus zeamais.
Mandibular gland secretions of meliponine worker bees: further evidence for their role in interspecific and intraspecific defence and aggression and against their role in food source signalling.
Volatile compounds in dry-cured Serrano ham subjected to high pressure processing. Effect of the packaging material.
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.
Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica.
Use of enantiomerically pure 7-azabicyclo[2.2.1]heptan-2-ol as a chiral template for the synthesis of aminocyclitols.
Enantioselective gas chromatographic analysis of aqueous samples by on-line derivatisation. Application to enzymatic reactions.
Identification of a sex pheromone produced by sternal glands in females of the caddisfly Molanna angustata curtis.
Enantioselective analysis of secondary alcohols and their esters in purple and yellow passion fruits.
Characterization of some mushroom and earthy off-odors microbially induced by the development of rot on grapes.
Chirality in anesthesia I: minimum alveolar concentration of secondary alcohol enantiomers.
Pollination by sexual mimicry in Mormolyca ringens: a floral chemistry that remarkably matches the pheromones of virgin queens of Scaptotrigona sp.
Mandibular gland secretion of Melipona beecheii: chemistry and behavior.
Purification and characterization of a novel alcohol dehydrogenase from Leifsonia sp. strain S749: a promising biocatalyst for an asymmetric hydrogen transfer bioreduction.
Electroantennography in the study of two stingless bee species (Hymenoptera: Meliponini).
Separation of enantiomers in microemulsion electrokinetic chromatography using chiral alcohols as cosurfactants.
[Chemical components of essential oils from the herb of Ligularia virgaurea].
Simple calculation for compounds lost by gas stripping in a two-phase liquid system involving dilute substances.
1. In vivo aroma release during eating of a model cheese: relationships with oral parameters.
Identification and synthesis of 2-heptanethiol, a new flavor compound found in bell peppers.
Behaviour of dehydrated baker's yeast during reduction reactions in a biphasic medium.
Microbial/enzymatic synthesis of chiral drug intermediates.
Secretions of stingless bees: cephalic secretions of two Frieseomelitta species.
Receptor neuron responses to potential sex pheromone components in the caddisfly Rhyacophila nubila (Trichoptera: Rhyacophilidae).
Enzymatic synthesis of aroma compound xylosides using transfer reaction by Trichoderma longibrachiatum xylanase.
Influence of octanoic acid addition to medium on some volatile compounds and PR-toxin biosynthesis by Penicillium roqueforti.
Solvent effect on ion-pair extraction of 2-(2-pyridylazo)-1-naphthol-4-sulfonate anion with solvated hydroxonium ion using alcohols and 1-octanol/octane mixed solvents.
Specialized olfactory receptor neurons mediating intra- and interspecific chemical communication in leafminer moths Eriocrania spp. (Lepidoptera: Eriocraniidae).
Characterization of the 2-[(R)-2-hydroxypropylthio]ethanesulfonate dehydrogenase from Xanthobacter strain Py2: product inhibition, pH dependence of kinetic parameters, site-directed mutagenesis, rapid equilibrium inhibition, and chemical modification.
A comparison of lipase-catalysed ester and lactone synthesis in low-water systems: analysis of optimum water activity.
Aroma-active components in fermented bamboo shoots.
Aromatic profile of aqueous banana essence and banana fruit by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O).
Flavor production from a non-stick oil by moulds.
Volatile compounds released during ripening in Italian dried sausage.
Camphor-based alpha-bromo ketones for the asymmetric darzens reaction
Odour-impact compounds of Gorgonzola cheese.
Synthesis and stereochemical assignment of exo- and endo-7-methyl-7-azabicyclo[2.2.1]heptan-2-ol.
Rationalization of enantioselectivities in dialkylzinc additions to benzaldehyde catalyzed by fenchone derivatives.
Enzymatic reduction of a less water-soluble ketone in reverse micelles with NADH regeneration.
Biological activity of the essential oil of Myrcianthes sp. nov. "black fruit" from Monteverde, Costa Rica.
Biological monitoring of exposure to n-heptane by gas chromatographic mass spectrometric determination of its metabolites.
Pheromonal secretions from glands on the 5th abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera).
Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells.
[The effects of heptaminol chlorhydrate on neuromuscular transmission].
Seed-germination inhibition by volatile alcohols and other compounds associated withAmaranthus palmeri residues.
Volatile flavour compounds in heated blackberry juices.
Identification of volatile allelochemicals fromAmaranthus palmeri S. Wats.
Synthesis of enantiomerically enriched 2-heptanol and 3-octanol by microbial reductases ofCurvularia falcata andMucor species.
Anesthetic potencies of secondary alcohol enantiomers.
Identification of the n-heptane metabolites in rat and human urine.
Alarm substances of the stingless bee,Trigona silvestriana.
Synthesis and bronchodilator activity of endo-2-(2-cyclopentyl-2-hydroxy-2-phenyl)acetoxy-7-methyl-7- azabicyclo-[2.2.1]heptane methobromide, a potent and long-acting anticholinergic agent.
Identification of volatile metabolites of inhaled n-heptane in rat urine.
Synthesis and platelet aggregation inhibition activity of a series of enantiomeric bicyclo[3.2.0]heptane-6-oximinoacetic acids (1).
Mandibular glands of stingless bees (Hymenoptera: Apidae): Chemical analysis of their contents and biological function in two species ofMelipona.
Effect of 2-alkanols on the separation of geometric isomers of retinol in non-aqueous high-performance liquid chromatography.
Alarm responses caused by newly identified compounds derived from the honeybee sting.
Absorption, distribution, elimination and metabolism of 14C-heptaminol hydrochloride in rat.
Identification of volatile compounds in hybrids between raspberry (Rubus idaeus, L.) and arctic bramble (Rubus arciticus, L.).
[Pharmacodynamic study of 6-amino-2-methyl-2-heptanol hydrochloride (heptaminol hydrochloride or R.P. 2831). 3. Effects of heptaminol hydrochloride on post-barbiturate hypotension and cardiac insufficiency].
[Pharmacodynamic study of 6-amino-2-methyl-2-heptanol hydrochloride (heptaminol hydrochloride or R.P. 2831). II. Action of heptaminol hydrochloride on diuresis in the dog].
[Pharmacodynamic study of 6-amino-2-methyl-2-heptanol hydrochloride (heptaminol hydrochloride or R. P. 2831). I. Action of heptaminol hydrochloride on the cardiovascular and central nervous systems].
[Action of 6-amino-2-methyl-2-heptanol in the treatment of various experimental cardiovascular shock states].
[Current aspects of the pharmacodynamics of 6-amino-2-methyl-2-heptanol (R. P. 2831)].
[Study with the aid of intracellular microelectrodes of the action of a cardiotonic: 2-methyl-6-amino-2-heptanol on nodal tissue of dog heart].
[Pharmaceutical property of 2-amino-6-methyl-2-2-heptanol hydrochloride].
[Cardiotonic properties of an alphatic amino alcohol, 6-amino-2-methyl-2-heptanol].
[Cardiotonic, coronary dilator, diuretic and right hypotensive (pulmonary artery and right ventricle) properties of 2-methyl-6 amino-2 heptanol hydrochloride (2831 RP)].
[Effects on right ventricular pressure of 2-methyl-6-amino-2 heptanol hydrochloride (RP 2831)].
[Effect of 2-methyl-6-amino-2-heptanol hydrochloride (RP 2831) on the coronary circulation].
[Action of 2-methyl-6-amino-2-heptanol hydrochloride (RP 2831) on diuresis].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB012157
YMDB (Yeast Metabolome Database):YMDB01343
Export Tariff Code:2905.19.9090
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 116.20372009277
Specific gravity @ 25 °C
Pounds per Gallon 6.773 to 6.857
Refractive Index 1.414 to 1.424 @ 20 °C
Boiling Point 160 to 162°C @ 760 mm Hg
Vapor Pressure 0.886 mmHg @ 25 °C
Flash Point TCC Value 64.44 °C TCC
logP (o/w) 2.31
Solubility
alcohol Yes
ether Yes
water, 3569 mg/L @ 25 °C (est) Yes
water, 3270 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Citrus
fresh, lemongrass, herbal, sweet, floral, fruity, green
General comment At 100.00 %. fresh lemon grass herbal sweet floral fruity green
Flavor Type: Fruity
fruity, green, earthy, bitter
General comment Fruity green earthy bitter

Occurrences

Potential Uses

Applications
Odor purposes Earth, Fruit, Green, Herbal, Lemon
Other purposes Grass
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 21 - Harmful in contact with skin.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] 2580 mg/kg
(Eder et al., 1982a)

oral-rat LD50 2580 mg/kg
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.

Dermal Toxicity:
skin-rabbit LD50 1780 ul/kg
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-heptanol usage levels up to:
5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 6.80 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 5
Click here to view publication 5
average usual ppmaverage maximum ppm
baked goods: -15.00000
beverages(nonalcoholic): -0.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -10.00000
condiments / relishes: -80.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.50000
fruit ices: -0.50000
gelatins / puddings: -5.00000
granulated sugar: --
gravies: --
hard candy: -1.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: -12.00000
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 7 (FGE.07): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf

Flavouring Group Evaluation 7, Revision 1 (FGE.07Rev1): Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Scientific opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission
View page or View pdf

Flavouring Group Evaluation 7, Revision 2 (FGE.07Rev2) : Saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched-chain carboxylic acids from chemical group 5
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):543-49-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10976
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1987
WGK Germany:3
heptan-2-ol
Chemidplus:0000543497
EPA/NOAA CAMEO:hazardous materials
RTECS:543-49-7