101-86-0

Basic information

• Product Name: alpha-Hexylcinnamaldehyde
• Synonyms: FEMA 2569;HCA;JASMONAL H;HEXYLCINNAMALDEHYDE;HEXYL CINNAMIC ALDEHYDE;A-N-HEXYL-B-PHENYLACROLEIN;ALPHA-HEXYLCINNAMIC ALDEHYDE;ALPHA-HEXYLCINNAMALDEHYDE
• CAS NO: 101-86-0
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.32
• EINECS: 202-983-3
• Product Categories: Pharmaceutical Intermediates;aldehyde Flavor;Aldehydes;C10 to C21;Carbonyl Compounds;Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 101-86-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 174-176 °C15 mm Hg(lit.)
• Flash Point: 200 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000697mmHg at 25°C
• Refractive Index: n20/D 1.55(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: soluble0.005g/L at 25°C
• CAS DataBase Reference: alpha-Hexylcinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Hexylcinnamaldehyde(101-86-0)
• EPA Substance Registry System: alpha-Hexylcinnamaldehyde(101-86-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38-34-43-52/53
• Safety Statements: 26-36/37/39-45-36-36/37-61
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 2
• RTECS: GD6560000
• Hazardous Substances Data: 101-86-0(Hazardous Substances Data)

Usage

Description

α-Hexylcinnamaldehyde has a jasmine-like odor, particularly on dilution. May be synthesized by condensation of octylaldehyde with benzaldehyde.

Chemical Properties

Different sources of media describe the Chemical Properties of 101-86-0 differently. You can refer to the following data:
1. Hexyl cinnamaldehyde has a jasmine-like odor, particularly on dilution.
2. alpha-Hexylcinnamaldehyde is a yellow liquid with a mild, slightly fatty, floral, somewhat herbal odor, and a distinct jasmine note. Similarly to the ??-amyl homolog, ??-hexylcinnamaldehydemust be protected against oxidation by the addition of stabilizers. It is prepared in a manner similar to that of ??-amylcinnamaldehyde by alkaline condensation of excess benzaldehyde with octanal (instead of heptanal). ??-Hexylcinnamaldehyde is widely used in flower compositions (e.g., jasmine and gardenia) and, because of its stability to alkali, in soap perfumes.
3. Pale-yellow liquid; jasminelike odor, particularly on dilution. Soluble in most fixed oils and in mineral oil; insoluble in glycerol and in propylene glycol.

Occurrence

Reported found in cooked, scented rice.

Uses

Different sources of media describe the Uses of 101-86-0 differently. You can refer to the following data:
1. hexyl cinnamal is also known as hexyl cinnamic aldehyde. It is a fragrance that provides a floral, jasmine-like scent.
2. α-Hexylcinnamaldehyde 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. It has been also used as flavouring additive in food and pharmaceutical industry.

Definition

ChEBI: A member of the class of cinnamaldehydes carrying a hexyl substituent at the alpha-position.

Preparation

By condensation of octylaldehyde with benzaldehyde

Taste threshold values

Taste characteristics at 5 ppm: sweet, waxy, floral, green, citrus and fruity nuances

General Description

Solubilization of α-hexylcinnamaldehyde by the ionic surfactants, sodium dodecyl sulfate and dodecyltrimethylammonium chloride and a non-ionic surfactant such as dodecyl polyoxyethylene ethers has been investigated.

Hazard

Combustible.

Contact allergens

Hexyl cinnamic aldehyde is a fragrance allergen. Its presence has to be mentioned by name in cosmetics within the EU.

InChI:InChI=1/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12-

Synthetic route

Octanal (124-13-0) + benzaldehyde (100-52-7) → α-hexylcinnamaldehyde (101-86-0)

Conditions	Yield
With benzoic acid; L-proline In neat (no solvent) at 125℃; for 1h; Aldol Condensation; Inert atmosphere;	97%
With nitrogen; potassium hydroxide In methanol; water at 30℃; for 6h;	93.8%
With pyrrolidine In neat (no solvent) at 120℃; for 0.25h; Microwave irradiation;	90%

Octanal (124-13-0) + benzaldehyde (100-52-7) → 2-hexyl-2-decenal (13893-39-5) + α-hexylcinnamaldehyde (101-86-0)

Conditions	Yield
With p-toluene sulfonic acid impregnated on MCM-41 In neat (no solvent) at 125℃; for 13h; Inert atmosphere; Green chemistry;

α-hexylcinnamaldehyde (101-86-0) → α-hexylcinnamyl alcohol (53892-67-4)

Conditions	Yield
With tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; potassium carbonate In water; isopropyl alcohol at 100℃; under 22502.3 Torr; for 17h; Inert atmosphere;	98%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol at 82℃; for 6h; Inert atmosphere; Schlenk technique; chemoselective reaction;	96%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol at 82℃; for 6h; Inert atmosphere; Green chemistry;	96%

α-hexylcinnamaldehyde (101-86-0) → (±)-2-benzyl-1-octanol (107613-28-5)

Conditions	Yield
With sodium tetrahydroborate; palladium diacetate In methanol at 20℃; for 1h;	95%

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 3-phenyl-propionaldehyde (104-53-0)

Conditions	Yield
With bismuth (III) nitrate pentahydrate In ethanol at 100℃; for 12h; Temperature;	92%

α-hexylcinnamaldehyde (101-86-0) → α-hexylcinnamaldehyde-α-d1

Conditions	Yield
With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; water-d2; potassium acetate In dichloromethane at 50℃; for 12h;	92%

α-hexylcinnamaldehyde (101-86-0) → (±)-2-benzyl-1-octanol (107613-28-5) + trans-α-n-hexylcinnamic alcohol (53892-67-4)

Conditions	Yield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;	A 91% B n/a

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 2-(1-phenyl-2-octyl)quinazolin-4(3H)-one

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 120℃; for 12h; Inert atmosphere;	88%

α-hexylcinnamaldehyde (101-86-0) + aniline (62-53-3) + propynoic acid ethyl ester (623-47-2) → ethyl 5-hexyl-1,4-diphenyl-1,4-dihydropyridine-3-carboxylate

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In toluene at 70℃; for 6h; Schlenk technique; Inert atmosphere;	84%

α-hexylcinnamaldehyde (101-86-0) + N-benzyloxy-α-methyl-α-bromopropionamide (1303507-75-6) → C26H33NO3

Conditions	Yield
With potassium hydroxide at 20℃;	84%

α-hexylcinnamaldehyde (101-86-0) + N-benzyloxy-α-methyl-α-bromopropionamide (1303507-75-6) → (E)-3-(benzyloxy)-5,5-dimethyl-2-(1-phenyloct-1-en-2-yl)-oxazolidin-4-one

Conditions	Yield
With potassium carbonate at 20℃;	84%

α-hexylcinnamaldehyde (101-86-0) + toluene-4-sulfonamide (70-55-3) → N-(2-hexyl-1H-inden-1-yl)-4-methylbenzenesulfonamide (1589518-79-5)

Conditions	Yield
With aluminum (III) chloride In nitromethane at 80℃; for 6h;	75%

3,5-dimethoxyphenol (500-99-2) + α-hexylcinnamaldehyde (101-86-0) → 3-hexyl-5,7-dimethoxy-2-phenyl-2H-chromene

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 120℃; for 16h; Schlenk technique; regioselective reaction;	72%

α-hexylcinnamaldehyde (101-86-0) + 2-Hydroxybenzoylhydrazine (936-02-7) → N'-(2-benzylideneoctylidene)-2-hydroxybenzohydrazide

Conditions	Yield
In ethanol at 60 - 70℃; for 8h;	69%

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 2-(1-benzylideneheptyl)-3H-quinazolin-4-one

Conditions	Yield
With bismuth (III) nitrate pentahydrate In ethanol at 100℃; for 12h;	68%

O-methylresorcine (150-19-6) + α-hexylcinnamaldehyde (101-86-0) → C22H26O2

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 130℃; for 16h; Schlenk technique; regioselective reaction;	63%

α-hexylcinnamaldehyde (101-86-0) + (E)-MeZnC(CH(Ph))B(pin) → C29H39BO3

Conditions	Yield
at -10℃; for 12h;	60%

α-naphthol (90-15-3) + α-hexylcinnamaldehyde (101-86-0) → C25H26O

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 130℃; for 12h; Schlenk technique; regioselective reaction;	59%

α-hexylcinnamaldehyde (101-86-0) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → N'-(2-benzylideneoctylidene)-4-hydroxybenzohydrazide

Conditions	Yield
In ethanol at 60 - 70℃; for 8h;	30%

α-hexylcinnamaldehyde (101-86-0) + benzyl alcohol (100-51-6) → 2-hexyl-3-phenyl-allyl alcohol (53892-67-4)

Conditions	Yield
With sodium hydroxide at 100℃;

1,5-dimethylhexylamine (543-82-8) + α-hexylcinnamaldehyde (101-86-0) → (1,5-Dimethyl-hexyl)-[2-[1-phenyl-meth-(E)-ylidene]-oct-(E)-ylidene]-amine (30121-85-8)

α-hexylcinnamaldehyde (101-86-0) + allyl bromide (106-95-6) → 1-Phenyl-2-hexyl-1,5-hexadien-3-ol (103826-27-3)

Conditions	Yield
With bismuth 1) DMF, r.t., 4 h, 2) r.t., 3 h; Yield given. Multistep reaction;
With bismuth 1.) DMF, room temperature, 2 h, 2.) DMF, room temperature, 2 h; Yield given. Multistep reaction;

α-hexylcinnamaldehyde (101-86-0) → allophanic acid-(2-hexyl-3-phenyl-allyl ester)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / 100 °C View Scheme

bromobenzene (108-86-1) + α-hexylcinnamaldehyde (101-86-0) → 1,3-diphenyl-2-n-hexyl-2-propen-1-ol

Conditions	Yield
With sodium hydrogencarbonate; magnesium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water

α-hexylcinnamaldehyde (101-86-0) → C29H39BO5

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C29H39BO4

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C23H28O4

Conditions	Yield
Multi-step reaction with 3 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C 3: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C23H28O4

Conditions	Yield
Multi-step reaction with 4 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C 3: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 0 °C 4: boron trifluoride diethyl etherate / tetrahydrofuran / 20 °C View Scheme

Triethoxysilane (998-30-1) + α-hexylcinnamaldehyde (101-86-0) → C21H36O4Si

Conditions	Yield
With C24H41FFeNP3 In tetrahydrofuran at 60℃; for 7h; Inert atmosphere; Schlenk technique;
With C18H37F5FeP4 In tetrahydrofuran at 40℃; Schlenk technique; Inert atmosphere;
With o-Ph2P(C6H4)Si(Me)2Fe(H)(PMe3)3 In tetrahydrofuran at 50℃; for 4h; Schlenk technique;
With 2C4H8O*C42H47FeOP5 In tetrahydrofuran at 60℃; for 36h; Inert atmosphere; Schlenk technique;

α-hexylcinnamaldehyde (101-86-0) → C30H33NO3S

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 1 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 4.1: potassium carbonate; gold(I) chloride / 1,2-dichloro-ethane / 60 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C37H39NO6S2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 1 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 4.1: potassium carbonate; gold(I) chloride / 1,2-dichloro-ethane / 60 °C View Scheme

Upstream product

• 124-13-0 Octanal 
• 100-52-7 benzaldehyde 

Downstream Products

• 104-53-0 3-phenyl-propionaldehyde 
• 1589518-79-5 N-(2-hexyl-1H-inden-1-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Α, β - production of unsaturated aldehydes

The present invention aims to provide a method for preparing an aldehyde, which can prepare a target aldehyde with high selectivity and can also suppress the production of by-products. The present invention relates to a method for preparing an α,β-unsaturated aldehyde. The method includes a step of reacting a compound of formula (I) with a compound of formula (II) to provide an α,β-unsaturated aldehyde of formula (III). An alkali metal hydroxide and an alkanol having 1 to 4 carbon atoms are used in the step. The amount of the alkali metal hydroxide is 8 mol% or more and 12 mol% or less with respect to the compound of formula (I). The total amount of water contained in materials that are used in the reaction is 10 mol% or more and 50 mol% or less with respect to the compound of formula (I).

Bifunctional organocatalysts for the synthesis of jasminaldehyde and their derivatives

L-Proline in the presence of benzoic acid is found to be an effective catalytic system for the cross-aldol condensation of benzaldehyde with 1-heptanal under solvent free condition amongst the several amino acids screened for this reaction. Under the optimized reaction conditions, the desired product (e.g. jasminaldehyde) is formed up to 96% selectivity in one hour using the desired arylaldehyde: 1-alkanaldehyde ratio as low as 2:1 under controlled addition of 1-alkanaldehyde.