1775-43-5

Basic information

• Product Name: CIS-3-HEXENOIC ACID
• Synonyms: (3Z)-3-Hexenoic acid;(Z)-3-Hexenoic acid;cis-Hydrosorbic acid;(Z)-11-Octadecenyl acetate;3-Hexenoic acid, (3Z)-;RARECHEM AL BE 0723;TIMTEC-BB SBB006610;FEMA 3170
• CAS NO: 1775-43-5
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 224-157-1
• Mol File: 1775-43-5.mol

Chemical Properties

• Boiling Point: 106-110 °C (16 mmHg)
• Flash Point: 108 °C
• Appearance: /
• Density: 0.965
• Vapor Pressure: 0.054mmHg at 25°C
• Refractive Index: 1.439-1.445
• CAS DataBase Reference: CIS-3-HEXENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-3-HEXENOIC ACID(1775-43-5)
• EPA Substance Registry System: CIS-3-HEXENOIC ACID(1775-43-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-25
• Hazardous Substances Data: 1775-43-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor Chemistry:
CIS-3-HEXENOIC ACID is used as a flavoring agent in the chemistry of flavors. Its unique chemical structure contributes to the development of distinct and complex flavor profiles, making it a valuable component in the creation of various food and beverage products.
Used in Fragrance Industry:
In the fragrance industry, CIS-3-HEXENOIC ACID is utilized as a key ingredient in the formulation of perfumes, colognes, and other scented products. Its ability to create unique and appealing aromas makes it an essential component in the development of new fragrances.
Used in Pharmaceutical Industry:
CIS-3-HEXENOIC ACID also finds applications in the pharmaceutical industry, where it is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties make it a valuable building block in the development of new medications and therapies.
Used in Cosmetic Industry:
In the cosmetic industry, CIS-3-HEXENOIC ACID is employed as an active ingredient in various skincare and beauty products. Its unique properties contribute to the development of innovative formulations that address specific skin concerns and enhance the overall appearance and health of the skin.

InChI:InChI=1/C6H10O2/c1-2-3-4-5-6(7)8/h4-5H,2-3H2,1H3,(H,7,8)/b5-4-

Upstream product

• 110-44-1 sorbic Acid 
• 86610-44-8 (Z)-5-Mercapto-3-hexenoic Acid 
• 6789-80-6 (3Z)-hexenal 
• 1002-28-4 3-hexyn-1-ol 
• 1918-79-2 2-methylthiophene-5-carboxylic acid 
• 75988-40-8 (Z)-5-(Ethylthio)-3-hexenoic Acid 
• 928-96-1 (Z)-3-Hexen-1-ol 
• 17814-72-1 pent-2-ynecarboxylic acid 

Downstream Products

• 13893-40-8 3-hydroxyhex-4-enoic acid 
• 76291-92-4 (E)-4-hydroxyhex-2-enoic acid 
• 98857-98-8 (Z)-3-hexenoic acid phenyl amide 
• 1373403-54-3 C₁₆H₂₂OS 

Relevant articles and documents

Directed, regiocontrolled hydroamination of unactivated alkenes via protodepalladation

A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized amino acids in good yields with high regioselectivity.

Structure-Odor Relationships of (Z)-3-Alken-1-ols, (Z)-3-Alkenals, and (Z)-3-Alkenoic Acids

(Z)-3-Unsaturated volatile acids, alcohols, and aldehydes are commonly found in foods and other natural sources, playing a vital role in the attractiveness of foods but also as compounds with chemocommunicative function in entomology. However, a systematic investigation of their smell properties, especially regarding humans, has not been carried out until today. To close this gap, the odor thresholds in air and odor qualities of homologous series of (Z)-3-alken-1-ols, (Z)-3-alkenals, and (Z)-3-alkenoic acids were determined by gas chromatography-olfactometry. It was found that the odor qualities in the series of the (Z)-3-alken-1-ols and (Z)-3-alkenals changed, with increasing chain length, from grassy, green to an overall fatty and citrus-like, soapy character. On the other hand, the odor qualities of the (Z)-3-alkenoic acids changed successively from cheesy, sweaty via plastic-like, to waxy in their homologous series. With regard to their odor potencies, the lowest thresholds in air were found for (Z)-3-hexenal, (Z)-3-octenoic acid, and (Z)-3-octenal.

Enantiodivergent and γ-selective asymmetric allylic amination

Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive. Copyright

Process for preparing cis alkenes and new catalysts therefor

In a method for preparation of cis-alkenes (I) by hydrogenating conjugated, non-cyclic dienes (II) in presence of homogeneously soluble transition metal catalyst (III), the new feature is that (III) is prepared in situ. In a method for preparation of cis-alkenes (I) by hydrogenating conjugated, non-cyclic dienes (II) in presence of homogeneously soluble transition metal catalyst (III), the new feature is that (III) is prepared in situ. (III) are of formulae (IIIa) or (IIIb). M = in (IIIa), a transition metal of Group VI in zero oxidation state, or in (IIIb) a metal of Group VIII in +2 oxidation state, Group IX in +1 oxidation state or Group X in +2 oxidation state; L1 = polydentate neutral or anionic ligand; L2 and L3 = together a conjugated, non-cyclic diene ligand; L4 = monodentate neutral ligand; L5 = polydentate neutral ligand; X = anion; and n = 1 or 2. Independent claims are also included for the following: (1) transition metal complex (C) for stereoselective hydrogenation of conjugated dienes to cisoid compounds that comprises a central ruthenium(II), an eta5 ligand, a bidentate, non-cyclic conjugated diene ligand and optionally a non-coordinating counterion for electrical neutrality, provided that when the ligand is pentamethylcyclopentadienyl (CpMe5) and the diene is sorbic acid, then the counterion is not triflate (trifluoromethylsulfonate) nor the BARF anion; and (2) methods for preparing specific (C).

An ionic liquid as catalyst medium for stereoselective hydrogenations of sorbic acid with ruthenium complexes

The ionic liquid 1-n-butyl-3-methylimidazolium hexafluorophosphate (bmim PF6) (6) has been studied as catalyst medium for biphasic homogeneous hydrogenations of sorbic acid (1). As catalyst we used the Cp*-ruthenium-complex [Cp*Ru(η4-CH3-CH=CH-CH=CH-COOH) (CF3SO3)] which efficiently enables the stereoselective hydrogenation of sorbic acid leading to the formation of cis-3-hexenoic acid (3) in selectivities of up to 90% with turnover frequencies of up to 1100 h-1. Compared to other biphasic systems the hydrogenation in bmim PF6 proceeds with enhanced activity. The kinetics can be described with a Michaelis-Menten-equation, and the activation energy for the whole process was determined to be EA = 78 ± 5 kJ/mol. Wiley-VCH Verlag GmbH, 2000.

Stereoselective catalytic hydrogenation of sorbic acid and sorbic alcohol with new Cp*Ru complexes

The new Cp*Ru complexes [Cp*Ru(η4-MeCH=CHCH=CHCO2H)]+X- (X- = CF3SO3- or [B{C6H3(CF3)2-3,5}4]-) are very effective catalysts for the hydrogenation of sorbic acid to cis-hex-3-enoic acid and of sorbic alcohol to cis-hex-3-en-1-ol (leaf alcohol) under mild conditions in liquid two-phase systems.

Selective two-phase-hydrogenation of sorbic acid with novel water soluble ruthenium complexes

Neutral and cationic water soluble Cp*-ruthenium-complexes of the type [Cp*Ru(CO)Cl(PR3)] and [Cp*Ru(CO)(PR3)]CF3SO3 (R=CH2OH, (CH2)3OH, Ph-m-SO3Na) have been synthesized for the first time and have been used as catalysts in two-phase-hydrogenations. The neutral complexes have been fully characterized. But the cationic complexes which have not been isolated are effective catalysts for the selective hydrogenation of sorbic acid in water/n-heptane leading to the formation of cis-3-hexenoic acid and trans-3-hexenoic acid.

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes.11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-epoxy esters

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the azidolysis of simple aliphatic cis and trans 2,3- and 3,4-epoxy esters and in the corresponding derivatives bearing an ether functionality (OBn) in an allylic relationship to the oxirane ring. The results indicate that the behavior of these epoxides is influenced both by the opening conditions (standard or metal-assisted) and the promoting metal salt [LiClO4 or Mg(ClO4)2]. Copyright

Rhodium(II)-vinylcarbenoid insertion into the Si - H bond. A new stereospecific synthesis of allylsilanes

Rh2(OAc)4 catalysed decomposition of vinyldiazocarbonyl compounds in the presence of organosilanes led stereospecifically to the corresponding allylsilanes in good yields. An asymmetric approach has also been considered as well as the extension of the methodology to the synthesis of other allylic systems.

Lithium/Ammonia Reductions of 2-Thiophenecarboxylic Acids

Lithium/ammonia reductions of 2-thiophenecarboxylic acids (1) in the absence of a proton source afforded mixtures of products.In the presence of methanol acyclic mercapto carboxylic acids (4) were the major products.Ring closure of 4 to the corresponding thiolactones (12) showed the double bonds in 4 to be of cis geometry.Attempts were made to prepare Z olefinic compounds derived from these mercapto carboxylic acids.Lithium 2-thiophenecarboxylate salts (2) afforded good yields of the corresponding 2,5-dihydro-2-thiophenecarboxylic acids (3).The presence of substituents on the ring and the ratio of metal to acid were significant factors in determining the nature of this products.A mechanism is proposed to explain the products observed.