Production Method 1

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ,  Silver Solvents: Ethanol ;  5.5 h, rt

Reference

Design of Core-Pd/Shell-Ag Nanocomposite Catalyst for Selective Semihydrogenation of Alkynes

Mitsudome, Takato; Urayama, Teppei; Yamazaki, Kenji; Maehara, Yosuke; Yamasaki, Jun; et al, ACS Catalysis, 2016, 6(2), 666-670

Production Method 2

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Dimethyl sulfoxide ,  Palladium Solvents: Hexane ;  210 min, 1 atm, 40 °C

Reference

Highly efficient Pd/SiO2-dimethyl sulfoxide catalyst system for selective semi-hydrogenation of alkynes

Takahashi, Yusuke; Hashimoto, Norifumi; Hara, Takayoshi; Shimazu, Shogo; Mitsudome, Takato; et al, Chemistry Letters, 2011, 40(4), 405-407

Production Method 3

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Formic acid Catalysts: Quinuclidine ,  Gold (amino-functionalized silica-supported) Solvents: Acetone ;  15 h, 60 °C

Reference

Gold-amine cooperative catalysis for reductions and reductive aminations using formic acid as hydrogen source

Fiorio, Jhonatan L. ; Araujo, Thaylan P.; Barbosa, Eduardo C. M.; Quiroz, Jhon; Camargo, Pedro H. C.; et al, Applied Catalysis, 2020, 267,

Production Method 4

764-60-3

928-94-9

Reaction Conditions

1.1 Catalysts: Copper ,  Titania (copper-modified) Solvents: Isopropanol ;  3 h, 298 K

Reference

Copper-Modified Titanium Dioxide: A Simple Photocatalyst for the Chemoselective and Diastereoselective Hydrogenation of Alkynes to Alkenes under Additive-Free Conditions

Kominami, Hiroshi; Higa, Megumi; Nojima, Taketo; Ito, Tomohiko; Nakanishi, Kousuke; et al, ChemCatChem, 2016, 8(12), 2019-2022

Production Method 5

1092696-25-7

928-94-9

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  rt

Reference

Enantiocontrolled Synthesis of Polychlorinated Hydrocarbon Motifs: A Nucleophilic Multiple Chlorination Process Revisited

Yoshimitsu, Takehiko; Fukumoto, Naoya; Tanaka, Tetsuaki, Journal of Organic Chemistry, 2009, 74(2), 696-702

Production Method 6

1577-28-2

928-94-9

Reaction Conditions

1.1 Solvents: Diethyl ether

Reference

Partial reduction of the double bond in 2-hexenoic acid by lithium aluminum hydride

Freedman, Robert W.; Becker, Ernest I., Journal of the American Chemical Society, 1951, 73, 2366-7

Production Method 7

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Nickel acetate Solvents: Methanol ;  0 °C
1.2 Reagents: Ethylenediamine ;  15 min, 0 °C
1.3 Reagents: Hydrogen ;  4 h, rt

Reference

Construction of Chemical Libraries of Volatile Compounds by Combinatorial Synthesis of Homologous Mixtures: Alk-4-en-1-ols, Alk-4-enals and Methyl Alk-4-enoates

Perrin, Coline; Baldovini, Nicolas, Chemistry & Biodiversity, 2023, 20(2),

Production Method 8

13894-64-9

928-94-9

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ,  Toluene ;  1 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  neutralized, -78 °C

Reference

Broad-Spectrum Cyclopropane-Based Inhibitors of Coronavirus 3C-like Proteases: Biochemical, Structural, and Virological Studies

Dampalla, Chamandi S. ; Nguyen, Harry Nhat; Rathnayake, Athri D. ; Kim, Yunjeong; Perera, Krishani Dinali ; et al, ACS Pharmacology & Translational Science, 2023, 6(1), 181-194

Production Method 9

27829-71-6

928-94-9

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Dichloromethane ;  -78 °C; -78 °C → rt; 2 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  15 min, 0 °C

Reference

Remote Stereocenter through Amide-Directed, Rhodium-Catalyzed Enantioselective Hydroboration of Unactivated Internal Alkenes

Zhao, Wei; Chen, Ke-Zhi; Li, An-Zhen; Li, Bi-Jie, Journal of the American Chemical Society, 2022, 144(29), 13071-13078

Production Method 10

16635-54-4

928-94-9

Reaction Conditions

1.1 Reagents: Sodium borohydride Catalysts: Methanesulfonic acid, 1,1,1-trifluoro-, erbium(3+) salt (3:1) Solvents: 2-Methyltetrahydrofuran ;  5 min, rt
1.2 Reagents: Water ;  rt

Reference

Eco-friendly stereoselective reduction of α,β-unsaturated carbonyl compounds by Er(OTf)3/NaBH4 in 2-MeTHF

Nardi, Monica; Sindona, Giovanni; Costanzo, Paola; Oliverio, Manuela; Procopio, Antonio, Tetrahedron, 2015, 71(7), 1132-1135

Production Method 11

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Gold (gold(core) supported with CeO2(shell)) Solvents: Toluene ;  15 h, 50 atm, rt

Reference

One-step Synthesis of Core-Gold/Shell-Ceria Nanomaterial and Its Catalysis for Highly Selective Semihydrogenation of Alkynes

Mitsudome, Takato; Yamamoto, Masaaki; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; et al, Journal of the American Chemical Society, 2015, 137(42), 13452-13455

Production Method 12

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Piperazine ,  Hydrogen Catalysts: Gold (poly(vinyl alc.) stabilized and carbon supported) Solvents: Ethanol ;  24 h, 6 bar, 80 °C

Reference

Piperazine-promoted gold-catalyzed hydrogenation: the influence of capping ligands

Fiorio, Jhonatan L.; Barbosa, Eduardo C. M.; Kikuchi, Danielle K.; Camargo, Pedro H. C.; Rudolph, Matthias; et al, Catalysis Science & Technology, 2020, 10(7), 1996-2003

Production Method 13

106498-75-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Triethyl phosphite ,  Gold Solvents: Isopropanol ;  30 h, 8 bar, 100 °C

Reference

Clean protocol for deoxygenation of epoxides to alkenes via catalytic hydrogenation using gold

Fiorio, Jhonatan L.; Rossi, Liane M., Catalysis Science & Technology, 2021, 11(1), 312-318

Production Method 14

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Lead ,  Palladium

Reference

Compounds with the aroma of green vegetables. V. Unbranched primary Z-alkenols

Vasil'ev, A. A.; Cherkaev, G. V.; Nikitina, M. A., Zhurnal Organicheskoi Khimii, 1993, 29(5), 889-94

Production Method 15

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Quinoline ,  Palladium Solvents: Hexane

Reference

Pheromone synthesis. 97. Synthesis of both the enantiomers of invictolide. A pheromone component of the red imported fire ant

Mori, Kenji; Nakazono, Yutaka, Tetrahedron, 1986, 42(23), 6459-64

Production Method 16

764-60-3

928-94-9

Reaction Conditions

1.1 Reagents: Quinoline ,  Hydrogen Catalysts: Palladium Solvents: Hexane

Reference

Palladium catalyzed thiocarbonylation and related reactions of functionally substituted alkenes and alkynes, allenes, and enynes

Xiao, Wen-Jing, 2001, , 62(4),

Production Method 17

4798-44-1

928-94-9

Reaction Conditions

1.1 Reagents: (T-4)-Trioxo(1,1,1-triphenylsilanolato)rhenium

Reference

(Trimethylsilyloxy)trioxorhenium

Young, David, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 18

928-94-9

Reaction Conditions

Reference

Synthesis of regioselectively deuterated cyclopropanes

Duffault, Jean-Marc; Hanoteau, Pascal; Parrilla, Alfredo; Einhorn, Jacques, Synthetic Communications, 1996, 26(17), 3257-3265

Production Method 19

928-94-9

Reaction Conditions

Reference

Efficient and regiocontrolled nickel(II)-catalyzed alkylation of 2-alkyl-1,3-dioxep-4-enes by Grignard reagents: a simple route to allylic alcohols

Malanga, Corrado; Menicagli, Rita; Lardicci, Luciano, Gazzetta Chimica Italiana, 1992, 122(1), 45-50

Production Method 20

928-94-9

Reaction Conditions

Reference

On the hydrozirconation of 4,4-dimethyl-2-oxazolines of some α,β-, β,γ- and γ,δ-unsaturated fatty acids

Alvhaell, J.; Gronowitz, S.; Hallberg, A.; Svenson, R., Chemica Scripta, 1984, 24(4-5), 170-7

cis-2-Hexen-1-ol Raw materials

• Oxiranemethanol, 3-propyl-
• 2-Hexenoic acid, (2Z)-
• 2-Hexyn-1-ol
• Benzene, 1,1'-[(1,1-dimethylethyl)[(2Z)-2-hexen-1-yloxy]silylene]bis-
• 2-Hexenoic acid, ethyl ester, (Z)-
• hex-1-En-3-ol
• 2-Hexenal, (2Z)-
• 2-Hexenoic acid, methyl ester, (Z)-

cis-2-Hexen-1-ol Preparation Products

• cis-2-Hexen-1-ol (928-94-9)

• 1. An approach to the structure and vibrational analysis of cis- and trans-3-chlorostyrene through IR/Raman and INS spectroscopies and theoretical ab initio/DFT calculations?
  J. M. Granadino-Roldán,M. Fernández-Gómez,A. Navarro,T. Pe?a Ruiz,U. A. Jayasooriya Phys. Chem. Chem. Phys., 2004,6, 1133-1143
• 2. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514
• 3. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
• 4. An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer?
  Xiaofeng Lin RSC Adv., 2016,6, 9002-9006
• 5. An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting?
  Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei Huang J. Mater. Chem. A, 2020,8, 12518-12525

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Exploring cis-2-Hexen-1-ol (CAS No. 928-94-9): Properties, Applications, and Industry Insights

cis-2-Hexen-1-ol, identified by its CAS number 928-94-9, is a naturally occurring unsaturated alcohol with a distinctive grassy, leafy aroma. This compound, also known as leaf alcohol, plays a pivotal role in flavor and fragrance formulations. Its molecular structure (C6H12O) features a cis-configuration at the double bond, which significantly influences its olfactory characteristics. The growing demand for natural and sustainable ingredients in cosmetics and food industries has propelled research into green synthesis methods for this molecule.

In recent years, cis-2-Hexen-1-ol has gained attention for its potential in biobased product development, aligning with the global shift toward circular economy principles. Analytical studies using GC-MS techniques confirm its presence in numerous plant species, including tea leaves and fresh fruits, where it contributes to fresh green notes. The compound's low odor threshold (0.25 ppb) makes it invaluable for creating realistic nature-identical flavors, particularly in beverages and dairy products.

The pharmaceutical sector has explored 928-94-9 as a chiral building block for asymmetric synthesis, leveraging its stereochemical purity. Advanced enzymatic resolution methods now enable production with >99% enantiomeric excess, meeting stringent regulatory requirements. Environmental studies highlight its rapid biodegradation (OECD 301F: 85% in 28 days), positioning it as an eco-friendly alternative to synthetic aroma chemicals.

Market trends reveal increasing applications in functional fragrances for aromatherapy products, where cis-2-Hexen-1-ol enhances stress-relief formulations. Recent patents demonstrate innovative uses in controlled-release systems for air care products, capitalizing on its volatility profile. The compound's QSAR (Quantitative Structure-Activity Relationship) data supports its safety profile, with LD50 values >2000 mg/kg (oral, rat).

Emerging research explores synergistic effects with other terpenes in plant defense mechanism simulations, offering potential for agricultural applications. Analytical challenges in stereoisomer separation have been addressed through novel HPLC chiral columns, ensuring product quality. The global market for cis-2-hexenyl derivatives is projected to grow at 6.2% CAGR through 2030, driven by demand in Asia-Pacific flavor markets.

Technical advancements in metabolic engineering now allow microbial production of 928-94-9 from renewable feedstocks, achieving titers of 15 g/L in optimized bioreactors. This aligns with UN Sustainable Development Goals for responsible consumption. The compound's partition coefficient (log P 1.62) makes it ideal for emulsion-based delivery systems, expanding applications in personal care products.

Recent consumer preference studies indicate cis-2-Hexen-1-ol ranks among top clean-label ingredients for savory snacks. Its EU Flavor Directive compliance (FL-no: 02.012) ensures broad regulatory acceptance. Innovations in encapsulation technologies have extended its shelf life in dry food applications, addressing historical stability challenges.

• 84117-75-9(2,6-Octadiene-1,8-diol, (Z,Z)-)
• 97259-62-6(2,6-Octadien-1-ol,(E,Z)- (9CI))
• 106310-19-4(Benzene, 4-isocyanato-2-methyl-1-[4-[(trifluoromethyl)thio]phenoxy]-)
• 7786-44-9(2,6-Nonadien-1-ol)
• 5820-89-3(2,6-Nonadien-1-ol,(E,E)- (8CI,9CI))
• 28069-72-9(trans,cis-2,6-Nonadien-1-ol)
• 2305-21-7(2-Hexen-1-ol)
• 928-95-0((E)-Hex-2-en-1-ol)
• 62019-06-1(2,6-Heptadien-1-ol, (2E)-)
• 24532-11-4(2,6-Octadien-1-ol)