Alpha-Ionone supplier | CasNO.127-41-3

Name
Alpha-Ionone
EINECS 204-841-6
CAS No. 127-41-3
Article Data65
CAS DataBase
Density 0.935 g/cm³
Solubility insoluble in water
Melting Point 59 - 61oC
Formula C₁₃H₂₀O
Boiling Point 257.604 °C at 760 mmHg
Molecular Weight 192.301
Flash Point 111.901 °C
Transport Information
Appearance clear yellow liquid
Safety 24/25-26-36/37/39-27
Risk Codes 42-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Alpha Ionone , Natural;4-(2, 6, 6-Trimethyl-2-cyclohexen-1-yl) 3-buten-2-one;Natural ionone alpha;(E)-(1)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one;4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one;(E)-4-[(1R)-2,6,6-trimethyl-1-cyclohex-2-enyl]but-3-en-2-one;
PSA 17.07000
LogP 3.51410

Synthetic route

: 141-10-6
pseudoionone

: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
With 3-methylbutyric acid; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride In toluene at -2 - 2℃; for 0.166667h; Reagent/catalyst; Temperature;	93.8%
With benzoic acid

: 472-78-6
α-ionol

: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
With butyltriphenylphosphonium dichromate In chloroform for 2h; Oxidation; Heating;	90%

: 64-18-6
formic acid

: 141-10-6
pseudoionone

: 127-41-3
alpha-ionone

: 141-10-6
pseudoionone

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
bei der Cyclisierung unter verschiedenen Bedingungen;

: 141-10-6
pseudoionone

: 64-19-7
acetic acid

: 127-41-3
alpha-ionone

: 14505-74-9, 41721-03-3, 59462-59-8, 432-24-6
α-cyclocitral

: 67-64-1
acetone

: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
With sodium ethanolate

: 141-10-6
pseudoionone

: 65-85-0
benzoic acid

: 127-41-3
alpha-ionone

: 62692-61-9
5E-6,10-dimethylundeca-3,5,9-trien-2-one

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
With lithium perchlorate; tetraethylammonium perchlorate In 1,2-dichloro-ethane at 55℃; for 0.416667h; electrolysis; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 2,6-dimethyl-undeca-1,5,8-triene

: 7664-93-9
sulfuric acid

: 64-19-7
acetic acid

: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

concentrated phosphoric acid: concentrated phosphoric acid

: 127-41-3
alpha-ionone

: 75-52-5
nitromethane

: 141-10-6
pseudoionone

: 7664-93-9
sulfuric acid

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
at -60 - 60℃; beim Behandeln eines Praeparats von ungewisser konfigurativer Einheitlichkeit;

...Expand

: 141-10-6
pseudoionone

: 7664-93-9
sulfuric acid

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

acid: acid

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 7446-70-0
aluminium trichloride

: 141-10-6
pseudoionone

CS2: CS2

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 7446-70-0
aluminium trichloride

: 141-10-6
pseudoionone

petroleum ether: petroleum ether

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

: 7732-18-5
water

ZnBr2: ZnBr2

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

: 64-19-7
acetic acid

ZnCl2: ZnCl2

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

: 7732-18-5
water

ZnI2: ZnI2

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

...Expand

: 141-10-6
pseudoionone

A: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

B: 127-41-3
alpha-ionone

C tricycloionone: tricycloionone

Conditions

Conditions	Yield
bei der Cyclisierung durch Saeuren;

...Expand

: 79-77-6
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

alcoholic potash: alcoholic potash

: 127-41-3
alpha-ionone

: 7664-93-9
sulfuric acid

: 13340-72-2, 50911-55-2
4-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one oxime

: 127-41-3
alpha-ionone

: 5392-40-5
(E/Z)-3,7-dimethyl-2,6-octadienal

: 127-41-3
alpha-ionone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium wire View Scheme

: C22H30O2

A: 127-41-3
alpha-ionone

B: 93-55-0
1-phenyl-propan-1-one

Conditions

Conditions	Yield
In methanol Irradiation;	A 95 %Spectr. B n/a

: 127-41-3
alpha-ionone

: trans-α-ionone 1,2-oxide

Conditions

Conditions	Yield
With Fe(bpmen)(OTf)2; dihydrogen peroxide; acetic acid In acetonitrile at 20℃; Concentration;	100%

: 127-41-3
alpha-ionone

: 1538551-03-9
C13H22O

Conditions

Conditions	Yield
With iron(III)-acetylacetonate; phenylsilane In ethanol at 60℃; for 0.25h;	98%

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 104-88-1
4-chlorobenzaldehyde

: 126-81-8
dimedone

: C28H34ClNO

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	92%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 126-81-8
dimedone

: 1122-91-4
4-bromo-benzaldehyde

: C28H34BrNO

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	90%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 104-87-0
4-methyl-benzaldehyde

: 126-81-8
dimedone

: C29H37NO

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	89%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 123-11-5
4-methoxy-benzaldehyde

: 126-81-8
dimedone

: C29H37NO2

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	86%

...Expand

: 127-41-3
alpha-ionone

: 31499-72-6
7,8-dihydro-α-ionone

Conditions

Conditions	Yield
With sodium dithionite; 2-methyldecanal; sodium hydrogencarbonate In 1,4-dioxane at 50℃;	85%
With ethanol; hydrogen; palladium
With hydrogen In tetrahydrofuran; methanol at 20℃; under 760.051 Torr;

: 127-41-3
alpha-ionone

: 190059-33-7
(E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one

Conditions

Conditions	Yield
With potassium superoxide; 2-Nitrobenzenesulfonyl chloride In acetonitrile at -35℃; for 3h;	85%

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 123-08-0
4-hydroxy-benzaldehyde

: 126-81-8
dimedone

: C28H35NO2

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	85%

...Expand

: 32806-04-5
diethyl methoxymethylphosphonic acid

: 127-41-3
alpha-ionone

: 1,5,5-trimethyl-6-(4-methoxy-3-methyl-1,3-butadienyl)-1-cyclohexene

Conditions

Conditions	Yield
Stage #1: diethyl methoxymethylphosphonic acid With potassium tert-butylate In N,N-dimethyl-formamide at -20℃; for 1.5h; Inert atmosphere; Stage #2: alpha-ionone In N,N-dimethyl-formamide at -20℃; for 1.5h; Reagent/catalyst; Solvent; Temperature; Wittig-Horner Reaction; Inert atmosphere;	83%

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 126-81-8
dimedone

: 139-85-5
3,4-dihydroxybenzaldehyde

: C28H35NO3

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	81%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 126-81-8
dimedone

: 100-83-4
meta-hydroxybenzaldehyde

: C28H35NO2

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	80%

...Expand

: 447-61-0
2-Trifluoromethylbenzaldehyde

: 127-41-3
alpha-ionone

: C21H23F3O

Conditions

Conditions	Yield
Stage #1: 2-Trifluoromethylbenzaldehyde; alpha-ionone With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	77%
sodium hydroxide In water

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 100-52-7
benzaldehyde

: 126-81-8
dimedone

: C28H35NO

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	77%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 90-02-8
salicylaldehyde

: 126-81-8
dimedone

: C28H35NO2

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	75%

...Expand

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 126-81-8
dimedone

: 121-33-5
vanillin

: C29H37NO3

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	75%

...Expand

: 127-41-3
alpha-ionone

: 616-38-6
carbonic acid dimethyl ester

: methyl 5-(2',6',6'-trimethylcyclohex-2'-enyl)-3-keto-4-pentenoate

Conditions

Conditions	Yield
With sodium hydride In toluene at 110℃; for 3h;	72%

: 127-41-3
alpha-ionone

: 631-61-8
ammonium acetate

: 126-81-8
dimedone

: 95-01-2
2,4-Dihydroxybenzaldehyde

: C28H35NO3

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120 - 130℃; for 2h; Sealed tube;	72%

...Expand

: 127-41-3
alpha-ionone

: 37677-81-9
4-(1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl)-3-buten-2-one

Conditions

Conditions	Yield
Stage #1: alpha-ionone With N-Bromosuccinimide; dimethyl sulfoxide at 10℃; for 0.5h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 0℃; for 0.5h; Inert atmosphere;	70%

: 67-56-1
methanol

: 127-41-3
alpha-ionone

: 127256-04-6
1,1-dimethoxy-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one

Conditions

Conditions	Yield
With ammonium persulfate; diphenyl diselenide for 3h; Heating;	65%

: 3,5-bis(trifluoromethyl)phenyl azide

: 127-41-3
alpha-ionone

: C21H23F6NO

Conditions

Conditions	Yield
With chloro[5,10,15,20-tetrakis(4-dimethylamino-2,3,5,6-tetrafluorophenyl)porphyrinate]iron(III) In 1,2-dichloro-ethane at 25 - 35℃; Irradiation; Molecular sieve; Sealed tube; Inert atmosphere;	60%

: 127-41-3
alpha-ionone

: 620-23-5
m-tolyl aldehyde

: C21H26O

Conditions

Conditions	Yield
Stage #1: alpha-ionone; m-tolyl aldehyde With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	55%

: 455-19-6
4-Trifluoromethylbenzaldehyde

: 127-41-3
alpha-ionone

: C21H23F3O

Conditions

Conditions	Yield
Stage #1: 4-Trifluoromethylbenzaldehyde; alpha-ionone With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	53%

: 127-41-3
alpha-ionone

: 99-61-6
3-nitro-benzaldehyde

: C20H23NO3

Conditions

Conditions	Yield
Stage #1: alpha-ionone; 3-nitro-benzaldehyde With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	53%

: 127-41-3
alpha-ionone

: 446-52-6
2-Fluorobenzaldehyde

: C20H23FO

Conditions

Conditions	Yield
Stage #1: alpha-ionone; 2-Fluorobenzaldehyde With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	52%

: 127-41-3
alpha-ionone

: 454-89-7
3-Trifluoromethylbenzaldehyde

: C21H23F3O

Conditions

Conditions	Yield
Stage #1: alpha-ionone; 3-Trifluoromethylbenzaldehyde With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	38%

: 127-41-3
alpha-ionone

: 146137-78-2
2-fluoro-5-trifluoromethylbenzaldehyde

: C21H22F4O

Conditions

Conditions	Yield
Stage #1: alpha-ionone; 2-fluoro-5-trifluoromethylbenzaldehyde With cetyltrimethylammonim bromide In water for 0.5h; Aldol condensation; Stage #2: With sodium hydroxide In water at 20℃; for 24h;	36%

: 127-41-3
alpha-ionone

: 93-55-0
1-phenyl-propan-1-one

: C22H30O2

Conditions

Conditions	Yield
Stage #1: 1-phenyl-propan-1-one With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate In dichloromethane for 0.25h; Inert atmosphere; Stage #2: alpha-ionone In dichloromethane Inert atmosphere;	30%

Alpha-Ionone Specification

The Alpha-Ionone, with the CAS registry number 127-41-3, is also known as (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one. It belongs to the product categories of Biochemistry; Monocyclic Monoterpenes; Terpenes; Intermediates & Fine Chemicals; Pharmaceuticals; Building Blocks; C13 to C14; Carbonyl Compounds; Chemical Synthesis; Citrus Aurantium (Seville orange); Ginkgo Biloba; Ketones; Nutrition Research; Organic Building Blocks; Phytochemicals by Plant (Food/Spice/Herb). Its EINECS registry number is 204-841-6. This chemical's molecular formula is C₁₃H₂₀O and molecular weight is 192.3. What's more, its IUPAC name is called (E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-3-en-2-one. It should be stored in a cool, dry and well-ventilated place. Alpha-Ionone is an aroma compound commonly found in essential oils such as rose oil. It is a degradation products of caratenoids produced by caratenoid cleavage dioxygenases (CCD).

Physical properties about Alpha-Ionone are: (1)ACD/LogP: 3.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.66; (4) ACD/LogD (pH 7.4): 3.66; (5)ACD/BCF (pH 5.5): 356.12; (6)ACD/BCF (pH 7.4): 356.12; (7)ACD/KOC (pH 5.5): 2333.67; (8)ACD/KOC (pH 7.4): 2333.67; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.512; (14)Molar Refractivity: 61.708 cm³; (15)Molar Volume: 205.659 cm³; (16)Polarizability: 24.463×10^-24cm³; (17)Surface Tension: 32.772 dyne/cm; (18)Density: 0.935 g/cm³; (19)Flash Point: 111.901 °C; (20)Enthalpy of Vaporization: 49.517 kJ/mol; (21)Boiling Point: 257.604 °C at 760 mmHg; (22)Vapour Pressure: 0.014 mmHg at 25 °C.

Uses of Alpha-Ionone: it is used to produce other chemicals. For example, it can react with trimethylaluminium to get 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentanone. This reaction needs reagent CuBr and solvents hexane, tetrahydrofuran. The reaction time is 2 hours. The yield is 90 %.

Alpha-Ionone can react with trimethylaluminium to get 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-pentanone.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes and may cause damage to health. And it is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In addition, you should avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(\C=C\C1C(=C/CCC1(C)C)\C)C
(2) InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
(3) InChIKey: UZFLPKAIBPNNCA-BQYQJAHWSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	2277mg/kg (2277mg/kg)		FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 46, 1967.

Product Name

Alpha-Ionone

Synthetic route

Alpha-Ionone Specification

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