HEXANAL

HEXANAL

Caproaldehyde = Hexyl aldehyde = Aldehyde C6

CAS: 66-25-1
European Community (EC) Number: 200-624-5
Molecular Formula: C6H12O
Molecular Weight: 100.16
IUPAC Name: hexanal
Linear Formula: CH3(CH2)4CHO

Boiling Point: 262 °F at 760 mm Hg, 129.6 °C
Melting Point: -58.2 °C
Flash Point: 90 °F 
25 °C (77 °F) - closed cup
90 °F (32 °C) Open cup
Solubility: 0.06 M
In water, 5.64X10+3 mg/L at 30 °C
In water, 0.6 wt% (6000 mg/L) at 20 °C
Very soluble in ethanol, ethyl ether; soluble in acetone, benzene
Miscible with alcohol, propylene glycol and most fixed oils
5.64 mg/mL at 30 °C
very slightly soluble in water; miscible with alcohol, propylene glycol, most fixed oils
Density: 0.83 at 68 °F
0.8335 g/cu cm at 20 °C
Bulk density = 6.9 wt/gal at 20 °C
0.808-0.817
Vapor Density: 3.45 (Air = 1)
Vapor Pressure: 11.26 mmHg
10.5 mm Hg at 20 °C
11.3 mm Hg at 25 °C

Hexanal is a volatile liquid aldehyde CH3(CH2)4CHO of irritating odor obtained from several volatile oils (as eucalyptus oil and peppermint oil).

Hexanal is a saturated fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde. 
It has a role as a human urinary metabolite. 
It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. 
It derives from a hydride of a hexane.

Hexaldehyde appears as a clear colorless liquid with a pungent odor. 
Flash point 90°F. 
Less dense than water and insoluble in water. 
Vapors heavier than air.

Hexanal, also called hexanaldehyde or caproaldehyde is an alkyl aldehyde used in the flavor industry to produce fruity flavors. 
Its scent resembles freshly cut grass, like cis-3-hexenal.
It is potentially useful as a natural extract that prevents fruit spoilage.
It occurs naturally, and contributes to a hay-like "off-note" flavor in green peas.

The first synthesis of hexanal was published in 1907 by P. Bagard.

Hexanal, once commonly called caproic aldehyde, is a six-carbon straight-chain aldehyde. 
It is a clear liquid with an atmospheric-pressure boiling point of 131 ºC. 
P. Bagard published the first synthesis of hexanal in 1907. 
It is found in foods ranging from olive oil to pears to Hass avocados. 
Its fruity flavor makes it a useful additive in the flavor industry.

A saturated fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde.

Hexanal, 1-hexanal, n-hexanal, is also known as caproaldehyde or hexanaldehyde. 
It belongs to the class of organic compounds known as medium-chain aldehydes which have a chain length between 6 and 12 carbon atoms and therefore is considered a fatty aldehyde lipid molecule. 
Hexanal is a very hydrophobic molecule that is relatively neutral. 
It is a colorless clear liquid. 
It has a fresh green, fatty or grassy scent with a green, fatty, leafy or aldehydic taste. 
Hexanal exists in all eukaryotes, from yeast to humans. 
Different foods contain hexanal with the highest concentrations found in black walnuts, corns, and tea and with lower concentrations in common grapes, thornless blackberries, and tortilla. Hexanal has also been detected in palms, mentha (mint), wax gourds, grapes, and kiwis making hexanal a potential biomarker for the consumption of these foods. 
Hexanal has been used to increase post-harvest longevity and color of certain fruits. 
Hexanal was also detected in humans breastmilk samples. 
Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. 
In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal, together with higher levels of 2-hydroxyhexanal and 4-hydroxynonena, are associated with poorer patient prognosis. 
Hexanal is a volatile compound that has been associated with the development of undesirable flavours and has been proposed as a potential marker of milk quality. 
Hexanal, a major breakdown product of linoleic acid oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods. 
A "cardboard-like" off-flavour is frequently associated with dehydrated milk products such as baby formulae and was correlated with the hexanal concentration.

Hexanal is an alkyl aldehyde found in human biofluids. 
Human milk samples collected from women contains hexanal. 
Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules.
Hexanal is a volatile compound that has been associated with the development of undesirable flavours. 
The content of hexanal, which is a major breakdown product of linoleic acid oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. 
A "cardboard-like" off-flavour is frequently associated with dehydrated milk products. 
This effect is highly correlated with the headspace concentration of hexanal. 

Consumer Benefits:

For consumers, the benefits of hexanal include fresher fruit, improvements in flavour and less wasted money. 
Fruits tested with hexanal in the Niagara region include nectarines and apples.

Nectarines are particularly prone to interior browning and mealiness, even when they look healthy and ripe from the outside. 
Field tests with nectarine trees demonstrated that a pre-harvest spray extended their shelf life by nine to 12 days, and delayed the browning and mealiness of the fruit.

Apples also taste better if they are allowed to ripen more on the trees.

Some popular varieties — like Honeycrisp — can develop a condition called bitter pit when in storage. 
This affects the way the apples look and makes them harder to sell. Hexanal helps prevent this.

There’s potential for using hexanal to improve the transportation of tastier fruit varieties that are currently too delicate to ship internationally.

Hexanal means the potential to improve farmers’ livelihoods. 
For example, tests in Tanzania found that using a pre-harvest spray reduced fruit falling from trees before harvest by 40 per cent.

In India, spraying mango trees allowed farmers to delay their harvests. 
This meant that rather than having to sell their mangoes during the seasonal market glut, farmers could sell them slightly later, resulting in an up to 40 per cent increase in their selling price.

Mango farmers in India also found that using the hexanal spray increased their harvest by about five kilograms a tree. 
In Sri Lanka, teams tested a post-harvest wax application, and found that it increased the shelf life of mangoes and papayas by up to 21 days.

In the Global South, small-scale fruit farmers are common. 
The prices farmers can get for their fruits are shaped by market conditions, the condition of the fruits and their ability to bargain with middle-men, markets and consumers.

Hexanal-based technologies help farmers to stretch the season and increase their bargaining power. 

Hexanal has been utilized in various fields including organic synthesis, rubber, paint, and additive in foods. 

Hexanal, sometimes referred to as aldehyde C-6, is a highly useful contributor to a veritable smorgasboard of green complexes. 
It adds an aspect of unripeness that can contribute significantly to the overall perception of freshness when it is used in moderation. 

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.

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.

A fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde.

SYNONYMS:

HEXANAL

Caproaldehyde

66-25-1

Hexaldehyde

Caproic aldehyde

Capronaldehyde

1-Hexanal

n-Hexanal

Hexanaldehyde

n-Caproaldehyde

Hexylaldehyde

Aldehyde C-6

Hexyl aldehyde

n-Capronaldehyde

n-Caproylaldehyde

Hexoic aldehyde

n-Hexaldehyde

C6 aldehyde

n-Caproic aldehyde

Kapronaldehyd

n-Hexylaldehyde

UNII-9DC2K31JJQ

NSC 2596

hexan-1-al

MFCD00007027

n-C5H11CHO

9DC2K31JJQ

CHEMBL280331

CHEBI:88528

DSSTox_CID_1604

Hexanal, 96%, stabilized

DSSTox_RID_76231

DSSTox_GSID_21604

Hexanal (natural)

Kapronaldehyd [Czech]

FEMA Number 2557

CAS-66-25-1

Aldehydes, C6

FEMA No. 2557

CCRIS 3219

HSDB 560

EINECS 200-624-5

UN1207

BRN 0506198

capronaidehyde

AI3-15364

1-hexanone

Aldehyde C6

PubChem3077

Hexanal, 98%

CCCC[CH]C=O

ACMC-1BFR4

EC 200-624-5

WLN: VH5

Hexanal, analytical standard

SCHEMBL22263

Caproaldehyde, Hexyl aldehyde

4-01-00-03296 (Beilstein Handbook Reference)

DTXSID2021604

NSC2596

Hexanal, natural, >=90%, FG

Hexanal, natural, >=95%, FG

Hexanal, >=97%, FCC, FG

NSC-2596

ZINC1641021

Tox21_201933

Tox21_303342

7134AH

ANW-35172

BDBM50028824

LMFA06000109

STL280331

AKOS009156478

EBD3061058

FS-3948

Hexanal 100 microg/mL in Acetonitrile

NE10466

UN 1207

NCGC00249137-01

NCGC00257270-01

NCGC00259482-01

DB-054893

FT-0631290

FT-0669191

Hexaldehyde [UN1207] [Flammable liquid]

EN300-33498

A835388

Q420698

J-660017

O8Y