// Workers AI · dad joke modeWhat did Cis-3-Hexen-1-ol say? "I'm bonded to you.
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| Names | |
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| Preferred IUPAC name
(3Z)-Hex-3-en-1-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.011.994 |
| EC Number |
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| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H12O | |
| Molar mass | 100.159 g/mol |
| Appearance | colorless liquid |
| Density | 0.846 g/cm3 |
| Melting point | −61 °C (−78 °F; 212 K) |
| Boiling point | 156.5 °C (313.7 °F; 429.6 K) |
| very slightly soluble | |
| Solubility | soluble in ethanol, ether |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 44 °C (111 °F) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
4700 mg/kg (rat, oral) |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves.[1] It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. It is prized for its intensely fresh, green, and natural character. And it is essential for creating authentic fruit, vegetable, and herbal flavour profiles. In fragrance formulation, cis-3-hexen-1-ol is essential for creating green, fresh, and outdoor-inspired scents, appearing in iconic perfumes such as Chanel No. 19 and Cristalle.
It has been evaluated by FDA, JECFA and International Fragrance Association.[2][3][4] The global production volume is about 3000 tonnes. Major cis-3-hexenol manufacturers include ZEON, NHU, and some Chinese companies like Sinofi.[5] Its esters are also important flavor and fragrance raw materials.
The related aldehyde cis-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated trans-2-hexenal.
This compound has been recognized as a semiochemical involved in mechanisms and behaviors of attraction in diverse animals such as insects and mammals.
Human odor perception
[edit]A pair of two single-nucleotide polymorphisms, both in the gene for the OR2J3 odor receptor, strongly reduce sensitivity to this odorant.[6]
Synthesis
[edit]In one of the syntheses, it is made by the Birch reduction of anisole starting material.[7]
References
[edit]- ↑ "(Z)-3-hexen-1-ol". scentsandflavors.com. Retrieved 31 July 2026.
- ↑ "Substances Added to Food (formerly EAFUS)". hfpappexternal.fda.gov. Retrieved 2026-08-25.
- ↑ "Food safety and quality: details". www.fao.org. Retrieved 2026-08-25.
- ↑ "Transparency List". IFRA. Retrieved 2026-08-25.
- ↑ "Buy Bulk - Cis-3-Hexenol | Manufacturer-Supplier". 2026-02-06. Retrieved 2026-08-25.
- ↑ McRae JF, Mainland JD, Jaeger SR, Adipietro KA, Matsunami H, Newcomb RD (2012). "Genetic Variation in the Odorant Receptor OR2J3 is Associated with the Ability to Detect the "Grassy" Smelling Odor, cis-3-hexen-1-ol". Chemical Senses. 37 (7): 585–593. doi:10.1093/chemse/bjs049. PMC 3408771. PMID 22714804.
- ↑ Dahill, R. T. (July 1972). "Convenient synthesis of cis-3-hexen-1-ol". Journal of Chemical & Engineering Data. 17 (3): 399–399. doi:10.1021/je60054a006.