3917-39-3

Basic information

• Product Name: ?-IONYLIDEN-ETHANOL
• Synonyms: ?-IONYLIDEN-ETHANOL;3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dien-1-ol;b-Ionyliden-ethanol
• CAS NO: 3917-39-3
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35
• Product Categories: Aliphatics;Retinoids;Aliphatics, Retinoids
• Mol File: 3917-39-3.mol

Chemical Properties

• Boiling Point: 329.06°C at 760 mmHg
• Flash Point: 123.208°C
• Appearance: /
• Density: 0.956g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ?-IONYLIDEN-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: ?-IONYLIDEN-ETHANOL(3917-39-3)
• EPA Substance Registry System: ?-IONYLIDEN-ETHANOL(3917-39-3)

Safety Data

• Hazardous Substances Data: 3917-39-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2E,4E)-β-Ionyliden-ethanol is used as a key intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to participate in a range of reactions, facilitating the formation of complex molecules and contributing to the development of new materials and products in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2E,4E)-β-Ionyliden-ethanol is used as a building block for the development of novel drugs. Its chemical properties make it suitable for the creation of new medicinal compounds, potentially leading to the discovery of innovative treatments for various diseases and conditions.
Used in Fragrance Industry:
(2E,4E)-β-Ionyliden-ethanol is also utilized in the fragrance industry as a component in the creation of unique and complex scents. Its distinctive chemical profile can contribute to the development of new perfumes and fragrances, enhancing the sensory experience for consumers.
Used in Chemical Research:
In the field of chemical research, (2E,4E)-β-Ionyliden-ethanol serves as a valuable compound for studying various reaction mechanisms and exploring new areas of chemical science. Its unique properties and reactivity make it an interesting subject for researchers, potentially leading to new discoveries and advancements in the field.

InChI:InChI=1/C15H24O/c1-12(9-11-16)7-8-14-13(2)6-5-10-15(14,3)4/h7-9,16H,5-6,10-11H2,1-4H3/b8-7+,12-9+

Upstream product

• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 62121-14-6 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienyl 4-nitrobenzoate 
• 20110-08-1 methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 144318-19-4 β-ionylideneethanol methyl ether 
• 99747-72-5 2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 
• 128426-10-8 (2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol 
• 55497-47-7 (e)-3-methyl-2-(2',6',6'-trimethylcyclohexenyl)-penta-1,3-diene 
• 121882-41-5 (2E)-3-methyl-3-tributylstannylprop-2-en-1-ol 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 475673-41-7 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl nonafluorobutanesulfonate 
• 37384-77-3 ethyl β-ionylidene acetate 
• 1856-65-1 (4E)-2-cyano-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienoic acid 
• 5299-98-9 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile 

Downstream Products

• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 7235-40-7 beta-carotene 
• 62285-98-7 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide 
• 3917-38-2 3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene 
• 885050-34-0 [9,10-13C₂]-11Z-retinol 
• 29443-88-7 (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol 
• 25576-25-4 (3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne 
• 68-26-8 vitamine A 
• 210700-51-9 ((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane 
• 17974-57-1 (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one 
• 347384-09-2 14,15-¹³C₂-retinoic acid ethyl ester 
• 103476-47-7 (2E,4Z,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenal 
• 53121-26-9 all-trans-13-demethyl-14-methylretinal 
• 128293-05-0 (E,E,E,E)-<2,7-Dimethyl-9-(2,6,6-trimethylcycloxhex-1-enyl)nona-2,4,6,8-tetraenyl>sulfonylbenzene 

Relevant articles and documents

INCORPORATION OF α-IONYLIDENE ETHANOL AND α-IONYLIDENE ACETIC ACID INTO ABSCISIC ACID BY CERCOSPORA ROSICOLA

2H-Labelled α-ionylidene ethanol and α-ionylidene acetic acid are converted in high yield to 1'-deoxy-abscisic acid (1'-deoxy-ABA) and abscisic acid (ABA) by Cercospora rosicola.Incorporation of label was confirmed by mass spectrometry.The 2-trans isomers

Syntheses of 13C2-labelled 11Z-retinals

To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann-Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of β-ionone with labelled triethyl phosphonoacetate.

Agents for use on skin and/or hair containing quadruply substituted cyclohexene compounds

The invention relates to agents for use on skin or hair, particularly for increasing skin tanning and the synthesis of melanin in skin or hair. The invention contains, in particular, cosmetic or dermatological preparations containing quadruply substituted

Accurate measurements of 13C-13C J-couplings in the rhodopsin chromophore by double-quantum solid-state NMR spectroscopy

A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance. Copyright

An efficient commercial process for the preparation of isotretinoin

We describe an efficient process for the preparation of isotretinoin (13-cis isomer of vitamin A acid) in a single step starting from β-ionylidene acetaldehyde (5). The process conditions are convenient to operate on a commercial scale and afford isotretinoin of excellent quality; levels of related isomeric impurities such as tretinoin (all trans retinoic acid) and 9,13-di-cis-retinoic acid are extremely low. Thus, condensation of dienolate of methyl 3,3-dimethylacrylate with β-ionylidene acetaldehyde (5) followed by aqueous acidic workup afforded isotretinoin in >95% purity. The condensation reaction proceeds via in situ formation of lactone (8); furthermore, the reaction conditions have been optimized to exploit in situ generated methoxide anion for lactone ring opening to afford the desired product. Distinct advantages of this process are that it does not require isolation of intermediate lactone and utilizes in situ generated methoxide for lactone ring opening, thus obviating the need for an additional step and base. We also describe an optimized process for the preparation of β-ionylidene acetaldehyde (5), a key intermediate for isotretinoin.

Palladium-catalyzed coupling reaction of an enol nonaflate with (vinyl)tributylstannanes and acetylenes: A highly stereoselective synthesis of 8,18-13C2-labeled retinal

Here we report that enol nonaflates exhibit higher reactivity than the corresponding enol triflates in palladium-catalyzed cross-coupling reactions with various (vinyl)tributylstannanes and acetylenes. We also highlight the reaction of a vinyl nonaflate,

Preparation and biological activity of 13-substituted retinoic acids

13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-inducing activity of ATRA in HL-60 cells. In contrast, in the 9Z-derivatives, all analogs, except for the 13-butyl derivatives, showed apoptosis-inducing activity.

Constraints of opsin structure on the ligand-binding site: Studies with ring-fused retinals

Ring-fused retinal analogs were designed to examine the hulatwist mode of the photoisomerization of the 9-cis retinylidene chromophore. Two 9-cis retinal analogs, the C11-C13 five-membered ring-fused and the C12-C14 five-membered ring-fused retinal derivatives, formed the pigments with opsin. The C11-C13 ring-fused analog was isomerized to a relaxed all-trans chromophore (λmax > 400 nm) at even - 269°C and the Schiff base was kept protonated at 0°C. The C12-C14 ring-fused analog was converted photochemically to a bathorhodopsin-like chromophore (λmax = 583 nm) at -196°C, which was further converted to the deprotonated Schiff base at 0°C. The model-building study suggested that the analogs do not form pigments in the retinal-binding site of rhodopsin but form pigments with opsin structures, which have larger binding space generated by the movement of transmembrane helices. The molecular dynamics simulation of the isomerization of the analog chromophores provided a twisted C11-C12 double bond for the C12-C14 ring-fused analog and all relaxed double bonds with a highly twisted C10-C11 bond for the C11-C13 ring-fused analog. The structural model of the C11-C13 ring-fused analog chromophore showed a characteristic flip of the cyclohexenyl moiety toward transmembrane segments 3 and 4. The structural models suggested that hula twist is a primary process for the photoisomerization of the analog chromophores.

Palladium catalyzed coupling reaction of an enol nonaflate with (vinyl)tributylstannanes and acetylenes

A novel method for a stereoselective synthesis of trienes and dienynes was developed by palladium catalyzed cross coupling reactions of an enol nonaflate with (vinyl)tributylstannanes and acetylenes in good to excellent yields. Here, the enol nonaflate ex

Synthesis of 10,11,14,15-13C4- and 14,15-13C2-retinyl acetate

The synthesis of 10,11,14,15-13C4- and 14,15-13C2-retinyl acetate is described. The procedure uses a modified Wittig-Horner synthesis. By using the 13C isotope, sensitive gas chromatography-combustion