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CAS Number: 101-86-0
IUPAC name: 2-Benzylideneoctanal
Chemical formula: C15H20O
EC Number: 202-983-3
Hexyl cinnamaldehyde (hexyl cinnamal) is a common additive in the perfume and cosmetic industry as aroma substance.
Hexyl cinnamaldehyde is found naturally in the essential oil of chamomile.
Hexyl cinnamaldehyde is a pale yellow to yellow liquid to solid, which is nearly insoluble in water but soluble in oils. The commercial material often contains low levels of 2,6-di-tert-butyl-4-methoxyphenol as a stabilizer.
One supplier reported that its hexyl cinnamaldehyde (or "hexyl cinnamic aldehyde") contained at least 90% trans isomer.
Synthesis
Hexyl cinnamaldehyde is typically produced via crossed-aldol condensation of octanal and benzaldehyde.
Safety
Hexyl cinnamaldehyde is known to cause contact allergies in some individuals but the rate of incidence is low, with patch tests indicating ~0.1% of people to be susceptible.
Alpha-hexylcinnamaldehyde is a member of the class of cinnamaldehydes carrying a hexyl substituent at the alpha-position. It is functionally related to an (E)-cinnamaldehyde.
Alpha-Hexylcinnamaldehyde is a natural product found in Plectranthus glabratus with data available.
Molecular Weight: 216.32
Density: 0.95 g/mL
Boiling point: 308 °C
Solubility in water: 2.75 mg/L
XLogP3-AA: 4.8
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 7
Exact Mass: 216.151415257
Monoisotopic Mass: 216.151415257
Topological Polar Surface Area: 17.1 Ų
Heavy Atom Count: 16
Complexity: 212
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
2-Hexylcinnamaldehyde, colloquially “hexyl cinnamal” and formally 2-(phenylmethylene)octanal, is a fragrance ingredient used in perfumes and personal-care products.
By itself, it has a jasmine-like odor.
2-Hexylcinnamaldehyde occurs naturally in chamomile oil, but almost all of the commercial product is synthesized via a reaction between octanal and benzaldehyde.
An antioxidant such as 2,6-di-tert-butyl-4-methoxyphenol (“butylated hydroxyanisole”) is usually added as a preservative.
Products & Informations
Hexyl cinnamaldehyde is found naturally in the essential oil of chamomile.
Hexyl cinnamaldehyde is a member of the class of cinnamaldehydes carrying a hexyl substituent.
Hexyl cinnamaldehyde industrially produced via a crossed-aldol condensation reaction between octanal and benzaldehyde.
USES
For the preparation of honey and fruit-type flavors and mixed spices;
used in soap and detergent;
Extraction solvents, mainly used in soybeans, rice bran, cottonseed and other edible oils and spices, such as oil resin extraction.
Used as intermediate of essence and fragrance, especially widely used in the essence of shampoo and hair care products.
Storage
Flammable materials should be stored in a separate safety storage cabinet or room
Ground all equipment containing material
Keep away from heat
Keep away from sources of ignition
Keep container tightly closed
Keep in a cool, well-ventilated place
Hexyl cinnamaldehyde is an aromatic chemical usually appearing as a pale yellow liquid with a sweet jasmine scent.
Though synthesized for industry, it is present naturally in chamomile (Chamaemelum nobile) essential oil.
Hexyl cinnamaldehyde is frequently used for its rich floral notes in the composition of fragrances for perfumery, personal care products and soaps.
Hexyl cinnamaldehyde is considered a low hazard when used at low concentrations.
Hexyl cinnamaldehyde is defined as a possible allergen by the EU Cosmetics Regulation, meaning a small percentage of people may be sensitive to this ingredient.
Alpha-Hexylcinnamaldehyde is used in fragrances for its floral scent.
While, today, manufacturers make it in a lab, alpha-hexylcinnamaldehyde is also found naturally in the essential oil of chamomile.
Hexyl cinnamaldehyde (hexyl cinnamal) is a pale yellow to yellow clear liquid to solid, which is nearly insoluble in water but soluble in oils.
Hexyl cinnamaldehyde is a common additive in perfume and cosmetic industry as aroma substance.
Hexyl cinnamaldehyde is found naturally in the essential oil of chamomile.
Many sites conflate amyl cinnamal, hexyl cinnamal and cinnamaldehyde (cinnamal/cinnamic aldehyde).
Hexyl cinnamal is not the same as amyl cinnamal, hexyl cinnamal has 6 carbons in the hydrocarbon chain whereas amyl cinnamal only has 5 carbons. The hydrocarbon chain in amyl cinnamal and hexyl cinnamal appears to lower the reactivity of the aldehyde group.
Hexyl cinnamaldehyde is an aromatic compound found naturally predominantly in chamomile.
However, Hexyl cinnamaldehyde can also be synthesized.
Hexyl cinnamaldehyde occurs as a yellowish aromatic liquid to solid with a characteristic odor.
Uses & Benefits
Hexyl cinnamaldehyde is mainly used as a fragrance and fixative ingredient.
Hexyl cinnamaldehyde can mix well with natural floral fragrances and gives a more natural and uniform fragrance.
Hexyl cinnamaldehyde can also be used in perfumes, skin creams, and foundations.
Hexyl cinnamaldehyde is a yellow liquid with a mild, slightly fatty, floral, somewhat herbal odor, and a distinct jasmine note.
Similarly to the amyl homolog, Hexyl cinnamaldehyde must be protected against oxidation by the addition of stabilizers.
Hexyl cinnamaldehyde is prepared in a manner similar to that of alpha-amylcinnamaldehyde by alkaline condensation of excess benzaldehyde with octanal (instead of heptanal).
Hexyl cinnamaldehyde is widely used in flower compositions (e.g., jasmine and gardenia) and, because of its stability to alkali, in soap perfumes.
Pale-yellow liquid; jasminelike odor, particularly on dilution.
Soluble in most fixed oils and in mineral oil; insoluble in glycerol and in propylene glycol.
Hexyl cinnamaldehyde is a fragrance that provides a floral, jasmine-like scent.
Uses
Hexyl cinnamaldehyde is characterized by a typical floral scent, which makes them suitable to be used as fragrances in personal care (perfumes, creams, shampoos, etc.) and household products.
Hexyl cinnamaldehyde has been also used as flavouring additive in food and pharmaceutical industry.
Solubilization of Hexyl cinnamaldehyde by the ionic surfactants, sodium dodecyl sulfate and dodecyltrimethylammonium chloride and a non-ionic surfactant such as dodecyl polyoxyethylene ethers has been investigated.
Hexyl cinnamaldehyde is a widely used fragrance chemical, the low skin-sensitizing potency of which has made it a common choice for the use as a positive control for predictive toxicology assays. However, Hexyl cinnamaldehyde is commonly negative in current candidate in vitro alternatives test methods.
Objective: To review the evidence that Hexyl cinnamaldehyde is a classifiable skin sensitizer against the standards set by the Globally Harmonized Scheme (GHS), and determine whether it represents an appropriate choice for a positive control substance for predictive testing.
Methods: Using the GHS criteria, mechanistic data, and in vitro, in vivo and human evidence relating to Hexyl cinnamaldehyde and skin sensitization have been reviewed.
Results: The chemistry of Hexyl cinnamaldehyde is consistent with potential for skin sensitization and predictive in vivo test data support this conclusion.
However, the human data are relatively sparse, consistent with Hexyl cinnamaldehyde possessing a low capacity to induce skin sensitization under conditions of consumer exposures.
Hexyl cinnamaldehyde is a chemical compound that belongs to the group of esters. It has been shown to be an effective biocide in vitro, with a response element of nitrogen atoms.
Hexyl cinnamaldehyde has a phase transition temperature of -44 degrees Celsius and can exist as both solid and liquid phases.
Hexyl cinnamaldehyde can be used for microextraction from biological samples, such as urine or blood, in combination with microcapsules.
Hexyl cinnamaldehyde has also been shown to have low potency against bacteria and fungi, but it is not toxic to mammals.
Beta-Hexyl cinnamaldehyde has similar properties.
Hexyl cinnamaldehyde has the warm spice and floral scent of flowers like jasmine and gardenia. In addition, also green spicy aspects.
The fragrance is not very strong and can therefore be used undiluted.
Typical use is in floral scents such as jasmine, magnolia and the like.
You usually use between 2% and 30% of this substance in the fragrance composition.
A very versatile fragrance: in addition to the floral scents mentioned, it also goes well with many fruit scents (especially berries and tropical fruits), in ambers.
Hexyl cinnamaldehyde is easy to underestimate because the fragrance only comes into its own in combination with other fragrances.
Hexyl cinnamaldehyde is primarily a base note in perfumes and is stable in most products, including soap. Keep cool, dry, dark and out of reach of children.
Hexyl cinnamaldehyde is a pale yellow to yellow liquid at room temperature. A better name might be alpha-Hexyl cinnamaldehyde, but since other variants are not used as fragrance, we leave that alpha out.
The purity is at least 96%. The substance has a fairly long shelf life.
The substance occurs in nature, but the synthetic version is used for use as a fragrance.
Hexyl cinnamaldehyde and p-tert-butyl-alpha-methylhydrocinnamic aldehyde are synthetic aldehydes, characterized by a typical floral scent, which makes them suitable to be used as fragrances in personal care (perfumes, creams, shampoos, etc.) and household products, and as flavouring additives in food and pharmaceutical industry.
Hexyl cinnamaldehyde is a weak allergen.
Other names:
alpha-Hexylcinnamaldehyde
Hexyl cinnamic aldehyde
101-86-0
Hexylcinnamaldehyde
(2E)-2-benzylideneoctanal
2-Benzylideneoctanal
165184-98-5
(E)-2-benzylideneoctanal
alpha-Hexylcinnamic aldehyde
2-(Phenylmethylidene)octanal
alpha-n-hexylcinnamaldehyde
(2E)-2-(phenylmethylidene)octanal
2-Hexyl-3-phenyl-2-propenal
alpha-Hexylcinnamyl aldehyde
Octanal, 2-(phenylmethylene)-
alpha-Hexyl-beta-phenylacrolein
CHEBI:55365
alpha-n-Hexyl-beta-phenylacrolein
2-Hexenyl cynnamaldehyde
2-(Phenylmethylene)octanal
alpha -hexylcinnamaldehyde
2-Hexylcinnamaldehyde
Hexylcinnamal
2-[(E)-benzylidene]octanal
E9947QRR9O
.alpha.-Hexylcinnamaldehyde
WLN: VHY6 & U1R
Hexyl cinnamic aldehyde (VAN)
hexyl cinnamal
n-Hexyl cinnamaldehyde
alpha-hexyl cinnamaldehyde
2-Hexyl-3-phenyl-propenal
.alpha.-Hexylcinnamic aldehyde
UNII-E9947QRR9O
Hexylzimtaldehyd
.alpha.-n-Hexyl-.beta.-phenylacrolein
alpha-Hexylcinnamaldehyde, (2E)-
alpha-hexylcinna-maldehyde
alfa-Hexyl Cinnam Aldehyde
Epitope ID:117426
EC 639-566-4
a-Hexylcinnamaldehyde, 8CI
2-(phenylmethylene)-octanal
alpha -hexylcinnamic aldehyde
MLS002174256
Cinnamaldehyde, alpha -hexyl-
SCHEMBL113170
Hexyl Cinnamic Aldehyde Natural
CHEMBL1449245
FEMA 2569
(2E)-alpha-n-hexylcinnamaldehyde
2-(Phenylmethylene)octanal, 9CI
DTXSID401020801
HMS3039O14
2-HEXYL-(E)-CINNAMALDEHYDE
NSC46150
ZINC4705576
alpha -N-hexyl-beta -phenylacrolein
BBL027629
MFCD00006989
NSC-46150
NSC406799
STK709222
(2Z)-2-Hexyl-3-phenyl-2-propenal
AKOS015839664
CS-W014834
HY-W014118
NSC-406799
NCGC00090930-01
NCGC00090930-02
alpha -N-hexyl-alpha -hexylcinnamaldehyde
LS-14416
Octanal, 2-(phenylmethylene)-, (2E)-
SMR001261427
VS-08571
EN300-18426
