66-25-1 Usage
Description
Hexanal has a characteristic fruity odor and taste (on dilution).
May be prepared from the calcium salt of caproic acid and formic
acid.
Chemical Properties
Different sources of media describe the Chemical Properties of 66-25-1 differently. You can refer to the following data:
1. Hexanal has a fatty, green, grassy, powerful, penetrating characteristic fruity odor and taste (on dilution).
2. Colorless liquid; sharp aldehyde odor.Immiscible with water.
3. Hexanal occurs, for example,
in apple and strawberry aromas as well as in orange and lemon oil. It is a colorless
liquid with a fatty, green odor and, in low concentration, is reminiscent of unripe
fruit.
Hexanal is used in fruit flavors and, when highly diluted, in perfumery for
obtaining fruity notes.
Occurrence
Reported found in some natural aromas of apple, strawberry, camphor oil, tea extracts, tobacco leaves,
Eucalyptus globulus, dwarf pine, bitter orange and coffee. Also reported found in nearly 300 natural sources including apple, apricot,
banana, sweet and sour cherry, citrus peel oils and juices, berries, guava, melon, raisins, peach, pear, papaya, pineapple, asparagus,
cabbage, celery, carrot, lettuce, shallots, onion, leek, ginger, parsley, bread, cheeses, butter, milk, fish, meats, cocoa, coffee, tea, nuts,
popcorn, potato chips, oat products, honey, soybean, plum, cauliflower, beetroot, celery root, figs, cardamom, coriander seed and leaf,
brussel sprouts, rice, quince, radish, lovage, corn oil, laurel and malt
Uses
Different sources of media describe the Uses of 66-25-1 differently. You can refer to the following data:
1. Hexanal occurs naturally inmany foods, such as in ripening
fruits, or because of addition as a flavorant; it has an apple taste. It can also be produced in foods because of lipid
peroxidation during cooking. It is mainly used as a food
flavorant, in fragrances, and in the manufacture of dyes,
plasticizers, synthetic resins, and pesticides. It is released to
air and water during production or use for the manufacture
of other products or during the use of these products
themselves. It undergoes oxidation and polymerization
readily.
Feron et al. identified hexanal in about 80 different
types of food.
2. Hexanal is used in the flavor industry to prepare fruity flavors. It is utilized as a flavoring agent in the food industry. It is also used in Witting and aldol reactions.
Definition
ChEBI: A fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde.
Preparation
Prepared from the calcium salt of caproic acid and formic acid
Aroma threshold values
Detection: 4.1 to 22.8 ppb; recognition: 400 ppb; aroma characteristics at 2.0%: green, fatty, leafy, vegetative, fruity and clean with a woody nuance
Taste threshold values
Taste characteristics at 2.5 ppm: green, woody, vegetative, apple, grassy, citrus and orange with a fresh,
lingering aftertaste
Synthesis Reference(s)
Journal of the American Chemical Society, 93, p. 1693, 1971 DOI: 10.1021/ja00736a021
General Description
A clear colorless liquid with a pungent odor. Flash point 90°F. Less dense than water and insoluble in water. Vapors heavier than air.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Caproaldehyde is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. May attack some forms of plastics [USCG, 1999].
Hazard
Flammable, moderate fire risk.
Health Hazard
Ingestion causes irritation of mouth and stomach. Contact with vapor or liquid irritates eyes. Liquid irritates skin.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: May attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Check Digit Verification of cas no
The CAS Registry Mumber 66-25-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 66-25:
(4*6)+(3*6)+(2*2)+(1*5)=51
51 % 10 = 1
So 66-25-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
66-25-1Relevant articles and documents
Photoactivated Oxidation of Alcohols by Oxygen
Cameron, Randy E.,Bocarsly, Andrew B.
, p. 6116 - 6117 (1985)
-
Manganese dioxide supported on aluminum silicate: A new reagent for oxidation of alcohols under heterogeneous conditions
Huang, Li-Hong,Ma, Yi-Chun,Zhang, Changhe,Wang, Qiang,Zou, Xiao-Nan,Lou, Ji-Dong
, p. 3377 - 3382 (2012)
Manganese dioxide supported on aluminum silicate, under heterogeneous conditions at reflux, selectively oxidized aromatic primary and secondary alcohols into the corresponding aldehydes and ketones, respectively, in yields of 87-96%. The present method failed to oxidize aliphatic alcohols.
Supported Au-Cu bimetallic alloy nanoparticles: An aerobic oxidation catalyst with regenerable activity by visible-light irradiation
Sugano, Yoshitsune,Shiraishi, Yasuhiro,Tsukamoto, Daijiro,Ichikawa, Satoshi,Tanaka, Shunsuke,Hirai, Takayuki
, p. 5295 - 5299 (2013)
Rejuvenating sunlight: Supported Au-Cu bimetallic alloy nanoparticles promote aerobic oxidation at room temperature under visible light (λ>450 nm) irradiation with little deactivation by the oxidation of surface Cu atoms by oxygen. This is achieved through the reduction of oxidized surface Cu atoms by the surface Au atoms, a process which is activated by visible-light irradiation, even by sunlight. Copyright
Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water
Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David
, (2021/11/30)
Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.
DIBALH: From known fundamental to an unusual reaction; Chemoselective partial reduction of tertiary amides in the presence of esters
An, Duk Keun,Heo, Yu Jin,Jaladi, Ashok Kumar,Kim, Hyun Tae
, p. 33809 - 33813 (2021/12/09)
This study presents a quick and reliable approach to the chemoselective partial reduction of tertiary amides to aldehydes in the presence of readily reducible ester groups using commercial DIBALH reagent. Moreover, the developed method was also extended to multi-functional molecules bearing ester moieties, which were successfully chemoselectively reduced to the corresponding aldehydes. This journal is
Synthesis of TEMPO radical decorated hollow porous aromatic frameworks for selective oxidation of alcohols
Shen, Yan-Ming,Xue, Yun,Yan, Mi,Mao, Hui-Ling,Cheng, Hu,Chen, Zhuo,Sui, Zhi-Wei,Zhu, Shao-Bin,Yu, Xiu-Jun,Zhuang, Jin-Liang
supporting information, p. 907 - 910 (2021/02/06)
A bottom-up approach was developed to prepare TEMPO radical decorated hollow aromatic frameworks (HPAF-TEMPO) by using TEMPO radical functionalized monomers and SiO2nanospheres as templates. The accessible inner layer, high density of TEMPO sites, and hybrid micro-/mesopores of the HPAF-TEMPO enable the aerobic oxidation of a broad range of alcohols with high efficiency and excellent selectivity.