2111-75-3

Basic information

• Product Name: (-)-PERILLALDEHYDE
• Synonyms: (-)-4-ISOPROPENYL-1-CYCLOHEXENE-1-CARBOXALDEHYDE;1-4(1-METHYLETHENYL)-1-CYCLOHEXANE-1-CARBOXALDEHYDE;L(-)-PERILLALDEHYDE;L-PERILLALDEHYDE;FEMA 3557;(S)-4-ISOPROPENYL-CYCLOHEX-1-ENECARBALDEHYDE;(S)-4-ISOPROPENYL-CYCLOHEXENE-1-CARBOXALDEHYDE;(S)-P-MENTHA-1,8-DIEN-7-AL
• CAS NO: 2111-75-3
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 218-302-8
• Product Categories: pharmacetical
• Mol File: 2111-75-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 104-105 °C10 mm Hg(lit.)
• Flash Point: 204 °F
• Appearance: /
• Density: 0.967 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0434mmHg at 25°C
• Refractive Index: n20/D 1.509
• Storage Temp.: 4°C, Light sensitive
• CAS DataBase Reference: (-)-PERILLALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-PERILLALDEHYDE(2111-75-3)
• EPA Substance Registry System: (-)-PERILLALDEHYDE(2111-75-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: GW2967200
• F: 10
• Hazardous Substances Data: 2111-75-3(Hazardous Substances Data)

Usage

Chemical Properties

p-Mentha-1,8-dien-7-al has a powerful fatty–spicy, oily, herbaceous odor.

Occurrence

Reported found in essential oils of bergamot, bilberries, gingergrass, lavender oil, loganberries, spearmint oil, Scotch spearmint oil, citrus peel oils, citrus juices, guava, blackberry, ginger, tea, calamus, caraway seed and mastic gum leaf oil, lime juice, lime peel oil, peppermint and black tea.

Uses

(±)-Perillaldehyde can be used as a bateriostatic agent.

Definition

ChEBI: An aldehyde that is cyclohex-1-ene-1-carbaldehyde substituted by a prop-1-en-2-yl group at position 4.

Preparation

By chromic oxidation of perilla alcohol.

Aroma threshold values

Detection: 30 to 62 ppb

Taste threshold values

Taste characteristics at 25 ppm: aromatic, orange, albedo, woody, spicy, waxy, sweet, citrus, lime and aldehydic.

InChI:InChI=1/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1

Synthetic route

perillol (536-59-4) → perillaldehyde (2111-75-3)

Conditions	Yield
With oxygen In 1,3,5-trimethyl-benzene at 60℃; under 760.051 Torr; for 4h; Solvent; Reagent/catalyst;	100%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; sodium chloride In 1,2-dichloro-ethane at 20℃; for 9h;	90%
With tert.-butylhydroperoxide; oxygen In decane; toluene at 80℃; under 750.075 Torr; Schlenk technique;	90%

2-nitro-benzaldehyde (552-89-6) → perillaldehyde (2111-75-3)

Conditions	Yield
With hydrogenchloride; aluminum isopropoxide In ethyl acetate; benzene	84%

l-perillic acid (7694-45-3) → perillaldehyde (2111-75-3)

Conditions	Yield
With Bis(N-methylpiperazinyl) aluminum hydride In tetrahydrofuran for 9h; Heating;	78%

perillol (536-59-4) → dihydroperilla alcohol (5502-72-7) + perillaldehyde (2111-75-3)

Conditions	Yield
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 2h; Ene Reaction;	A 40% B 60%

(+/-)-(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde (564-94-3, 18486-69-6, 23727-16-4, 57526-63-3) → perillaldehyde (2111-75-3)

Conditions	Yield
at 380 - 400℃; beim Leiten durch ein Eisen-Rohr;

1-Chlor-4-isopropenylcyclohexen (39850-85-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → perillaldehyde (2111-75-3)

Conditions	Yield
(i) Li, Et2O, (ii) /BRN= 605365/; Multistep reaction;

dihydrocuminyl alcohol → perillaldehyde (2111-75-3)

Conditions	Yield
With chromic acid levorotatory form;

levorotatory perilla alcohol → perillaldehyde (2111-75-3)

Conditions	Yield
With chromic acid levorotatory perillaldehyde;

(methyl)(4-chlorocyclohex-3-en-1-yl)ketone (41747-24-4) → perillaldehyde (2111-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: (i) Li, Et2O, (ii) /BRN= 605365/ View Scheme

limonene. (138-86-3) → perillaldehyde (2111-75-3)

Conditions	Yield
With sodium hydrogencarbonate; sodium sulfite In dichloromethane; 3-chloro-benzenecarboperoxoic acid

formaldehyd (50-00-0) + trans-Crotonaldehyde (123-73-9) + isoprene (78-79-5) → 3-methyl-1-vinylcyclohex-3-enecarbaldehyde (40398-14-9) + perillaldehyde (2111-75-3) + 4-methyl-1-vinylcyclohex-3-enecarbaldehyde (40398-47-8)

Conditions	Yield
With pyrrolidine; propionic acid In water at 100℃; for 16h; Autoclave;

perillaldehyde (2111-75-3) → perillol (536-59-4)

Conditions	Yield
With lithium pyrrolidinoborohydride at 25℃;	97%
Stage #1: perillaldehyde With [Ru(2-(ethylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate In isopropyl alcohol under 22502.3 Torr; Autoclave; Inert atmosphere; Stage #2: With hydrogen In isopropyl alcohol at 80℃; under 22502.3 Torr; for 1h;	96%
With bis(triphenylphosphine)copper(I) nitrate; hydrogen; 1,4-di(diphenylphosphino)-butane; sodium hydroxide In ethanol at 50℃; under 37503.8 Torr; for 16h; Autoclave; Inert atmosphere; chemoselective reaction;	92%

perillaldehyde (2111-75-3) + cyclopenta-1,3-diene (542-92-7) → 6-(4-Isopropenyl-1-cyclohexenyl)fulvene

Conditions	Yield
With pyrrolidine	97%

perillaldehyde (2111-75-3) + allylmagnesium bromide (1730-25-2) → 1-(1-hydroxy-3-butenyl)-4-(1-methylethenyl)-cyclohexene (95374-99-5)

Conditions	Yield
In diethyl ether	93%

chloro-trimethyl-silane (75-77-4) + perillaldehyde (2111-75-3) + diallyldibutyltin (15336-98-8) → [1-(4-Isopropenyl-cyclohex-1-enyl)-but-3-enyloxy]-trimethyl-silane

Conditions	Yield
In acetonitrile for 6h; Ambient temperature;	92%

perillaldehyde (2111-75-3) + ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate (663155-32-6) → ethyl 3-(4-isopropenylcyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-enoate

Conditions	Yield
Stage #1: ethyl 2-diphenylphosphono-3-(trimethylsilyl)propionate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: perillaldehyde In tetrahydrofuran at -60 - 20℃; for 14.5h; Ando-Horner-Wadsworth-Emmons reaction; -;	91%

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) + perillaldehyde (2111-75-3) → 3-hydroxy-3-(4-isopropenyl-cyclohex-1-enyl)-2,2-dimethyl-propionic acid methyl ester

Conditions	Yield
With pyridine N-oxide; lithium chloride In N,N-dimethyl-formamide at 20℃; for 10h;	91%
With 1-methyl-1H-imidazole; lithium chloride In N,N-dimethyl-formamide at 20℃; for 10h;	90%

perillaldehyde (2111-75-3) + aniline (62-53-3) → N-((4-(prop-1-en-2-yl)cyclohex-1-enyl)methyl)aniline

Conditions	Yield
With Dimethylphenylsilane In acetonitrile at 20℃; for 2h; Inert atmosphere; Green chemistry;	91%
Stage #1: perillaldehyde; aniline In methanol at 20℃; for 12h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2h; Cooling with ice;	89%
Stage #1: perillaldehyde; aniline In methanol for 24h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;

perillaldehyde (2111-75-3) + ethyl sodiodiethylphosphonoacetate (22822-85-1) → (E)-3-(4-Isopropenyl-cyclohex-1-enyl)-acrylic acid ethyl ester (516472-73-4)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	89.5%

perillaldehyde (2111-75-3) + N-butylamine (109-73-9) → p-perilla-7-n-butylamine

Conditions	Yield
Stage #1: perillaldehyde; N-butylamine In methanol at 20℃; for 12h; Stage #2: With methanol; sodium tetrahydroborate at 20℃; for 2h; Temperature; Reagent/catalyst; Cooling with ice;	88%
Stage #1: perillaldehyde; N-butylamine In methanol for 24h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;

perillaldehyde (2111-75-3) → [4-(1-methylethenyl)-1-cyclohexen-1-yl]methylamine (52209-34-4)

Conditions	Yield
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen In water at 120℃; for 24h; Autoclave;	87%

perillaldehyde (2111-75-3) → 4-isopropenylcyclohexene-1-carbonitrile (60188-94-5, 156555-45-2)

Conditions	Yield
With ammonia; oxygen In tert-Amyl alcohol at 40℃; under 750.075 Torr; for 24h; Green chemistry;	85%

4-phenylbut-1-en-3-yne (13633-26-6) + perillaldehyde (2111-75-3) → (1S,2R)-2-(phenylethynyl)-1-((S)-4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)propane-1,3-diol

Conditions	Yield
Stage #1: 4-phenylbut-1-en-3-yne; perillaldehyde With [(1S,4R)-3-[4-(diphenylphosphino)-2,5-dimethyl-3-thienyl]-4,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]diphenylphosphine; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 22℃; for 8h; Inert atmosphere; Glovebox; Stage #2: With sodium perborate tetrahydrate In tetrahydrofuran at 22℃; for 3h; Inert atmosphere; Glovebox;	79%

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0) + perillaldehyde (2111-75-3) → 2-(4-Isopropenyl-cyclohex-1-enyl)-4-methylene-tetrahydro-furan (99583-47-8)

Conditions	Yield
With triphenylphosphine; palladium diacetate In 1,4-dioxane Heating;	71%

perillaldehyde (2111-75-3) → perillol (536-59-4) + C20H30O2

Conditions	Yield
With acetic acid; zinc In water at 20℃; for 0.333333h; Green chemistry;	A 6% B 71%

perillaldehyde (2111-75-3) → C10H13ClO + C10H12Cl2O

Conditions	Yield
Stage #1: perillaldehyde With iron(III) chloride In dichloromethane; water at 20℃; Stage #2: With sodium hypochlorite In dichloromethane; water at 20℃; for 0.583333h;	A 68% B 30%

perillaldehyde (2111-75-3) → (4S)-(3-oxoprop-1-en-2-yl)cyclohex-1-enecarbaldehyde + 4-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-enecarbaldehyde

Conditions	Yield
With selenium(IV) oxide In ethanol for 18h; Heating;	A 66% B n/a

perfluorophenyl azide (1423-15-0) + perillaldehyde (2111-75-3) → C16H14F5NO

Conditions	Yield
With Co(3,5-DitBu-Ibu-Phyrin) In chlorobenzene at 80℃; for 24h; Molecular sieve;	50%

Dimethyldisulphide (624-92-0) + perillaldehyde (2111-75-3) → C11H18OS

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In 1,2-dichloro-ethane at 20℃; for 16h; Irradiation; regioselective reaction;	48%

perillaldehyde (2111-75-3) + 4-hydroxy-2-deoxy-2-thiocoumarin (70685-46-0) → (6aH)-7,8,9,10-tetrahydro-8-(prop-1-en-2-yl)-5-oxa-6-thia-naphthacen-12-one + (6aH)-9,10,11,11a-tetrahydro-10-(prop-1-en-2-yl)-chromeno[4,3-b]chromen-6-thione

Conditions	Yield
ytterbium(III) trifluoromethanesulphonate In methanol Knoevenagel reaction;	A 44% B 36%

Allyl acetate (591-87-7) + perillaldehyde (2111-75-3) → 1-(1-hydroxy-3-butenyl)-4-(1-methylethenyl)-cyclohexene (95374-99-5)

Conditions	Yield
With tetraethylammonium tosylate; zinc(II) chloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide electrochemical reduction;	42%

perillaldehyde (2111-75-3) + (S)-5-oxopyrrolidine-2-carbohydrazide (934-06-5) → 5-oxo-N'-((4-(prop-1-en-2-yl)cyclohex-1-en-1 yl)methylene)pyrrolidine-2-carbohydrazide

Conditions	Yield
With hydrazine hydrate In water at 20℃; for 1h;	40%

perillaldehyde (2111-75-3) + O,O-dimethyl bismethylphosphonate (114121-06-1) → (Z)-4-isopropenyl-1-(2-(dimethylphosphono)-2-(trimethylsilylvinyl))cyclohexene (1615248-95-7) + (E)-4-isopropenyl-1-(2-(dimethylphosphono)-2-(trimethylsilylvinyl))cyclohexene (1615248-94-6)

Conditions	Yield
Stage #1: O,O-dimethyl bismethylphosphonate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70℃; for 0.25h; Inert atmosphere; Stage #2: perillaldehyde In tetrahydrofuran; hexane at -70℃; for 0.25h; Peterson Olefination; Inert atmosphere; Stage #3: With benzoic acid methyl ester In tetrahydrofuran; hexane at 20℃; for 12h; Reagent/catalyst; Inert atmosphere;	A 24% B 18%
With benzoic acid methyl ester; lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 12.5h; Peterson Olefination; Inert atmosphere; Overall yield = 53 %;	A n/a B n/a

perillaldehyde (2111-75-3) + 3-methyl-2-buten-1-ol (556-82-1) → 3-(3-methylbut-2-en-1-yl)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde

Conditions	Yield
With triethylamine hydrochloride In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 16h; Inert atmosphere; Enzymatic reaction;	23%

perillaldehyde (2111-75-3) + sodium cyanide (143-33-9) + borontrifluoride acetic acid (753-53-7, 373-61-5) → Acetic acid 2-(4-isopropylidene-cyclohexyl)-ethyl ester

Conditions	Yield
Multistep reaction;

perillaldehyde (2111-75-3) → p-menth-3-en-7-ol (21425-79-6)

Conditions	Yield
(i) Li, liq. NH3, iPrOH, Et2O, (ii) aq. H2SO4; Multistep reaction;

Upstream product

• 39850-85-6 1-Chlor-4-isopropenylcyclohexen 
• 68-12-2 N,N-dimethyl-formamide 
• 552-89-6 2-nitro-benzaldehyde 
• 138-86-3 limonene. 
• 6931-54-0 β-pinene oxide 
• 177698-19-0 Beta-pinene 
• 7694-45-3 l-perillic acid 
• 536-59-4 perillol 
• 50-00-0 formaldehyd 
• 123-73-9 trans-Crotonaldehyde 
• 78-79-5 isoprene 
• 41747-24-4 (methyl)(4-chlorocyclohex-3-en-1-yl)ketone 
• 564-94-3 (+/-)-(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 

Downstream Products

• 7694-45-3 4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid 
• 1615248-95-7 (Z)-4-isopropenyl-1-(2-(dimethylphosphono)-2-(trimethylsilylvinyl))cyclohexene 
• 1615248-94-6 (E)-4-isopropenyl-1-(2-(dimethylphosphono)-2-(trimethylsilylvinyl))cyclohexene 
• 77142-27-9 4-(2-propenyl)-1-vinylcyclohexene 
• 122-03-2 (4-isopropylbenzaldehyde) 
• 95374-99-5 1-(1-hydroxy-3-butenyl)-4-(1-methylethenyl)-cyclohexene 
• 22451-49-6 trans-dihydroperillaldehyde 
• 22451-50-9 cis-dihydroperillaldehyde 
• 536-59-4 perillol 
• 101128-17-0 E-fluoro-2 (isoprene-1 yl)-4 (cyclohexene-1 yl)-3 propene-2 oate de methyle 
• 101128-18-1 Z-fluoro-2 (isoprene-1 yl)-4 (cyclohexene-1 yl)-3 propene-2 oate de methyle 
• 95636-67-2 Z-((isopropen-1-yl)-4-cyclohexen-1-yl)-3-methyl-2-propen-2-oate de methyle 
• 89996-96-3 E-((isopropen-1-yl)-4-cyclohexen-1-yl)-3-methyl-2-propen-2-oate de methyle 

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