cis-4-Hexen-1-ol: Properties, Handling & Lab Use Guide

cis-4-Hexen-1-ol is a six-carbon cis-unsaturated primary alcohol widely used in flavor, fragrance, and organic synthesis research.

IUPAC Name

(Z)-hex-4-en-1-ol

Molecular Formula

C₆H₁₂O

Molecular Weight

100.16 g/mol

CAS Number

928-91-6

Appearance

Colorless to pale yellow liquid

Key Application

Flavor & fragrance, organic synthesis intermediate

SKU

C153483

Physicochemical Properties

cis-4-Hexen-1-ol (CAS 928-91-6, IUPAC: (Z)-hex-4-en-1-ol) is a colorless to pale yellow liquid with a characteristic green, leaf-like odor profile. Its molecular formula is C₆H₁₂O and its molecular weight is approximately 100.16 g/mol. The compound possesses a terminal primary hydroxyl group (–OH) at C-1 and a cis (Z)-configured double bond between C-4 and C-5, making it structurally distinct from its trans isomer.

The cis geometry of the double bond confers lower boiling point and different solubility characteristics compared to fully saturated hexan-1-ol. The compound is miscible with common organic solvents such as ethanol, diethyl ether, and dichloromethane, and shows limited miscibility with water. The hydroxyl group renders the molecule amenable to a wide range of functional-group transformations including esterification, oxidation, and Mitsunobu reactions.

Research Applications

Flavor and Fragrance Chemistry: cis-4-Hexen-1-ol belongs to the family of C6 green-leaf alcohols found naturally in many fruits, vegetables, and plant tissues. It is used as a reference standard and synthetic building block in flavor science research. Its green, slightly fruity odor character makes it relevant to studies investigating plant volatile biosynthesis, food aroma profiling, and consumer sensory evaluation.

Organic Synthesis: The combination of a primary allylic alcohol and a cis-double bond provides two distinct reactive handles. Researchers use cis-4-Hexen-1-ol as an intermediate for the preparation of esters, carbonates, and halide derivatives. The alkene moiety can participate in epoxidation (e.g., Sharpless asymmetric epoxidation), dihydroxylation, cross-metathesis, and hydroboration sequences. The resulting chiral or functionalized products serve as intermediates in the synthesis of bioactive natural products and pharmaceutically relevant molecules.

Chemical Ecology: C6 unsaturated alcohols are part of the green leaf volatile (GLV) blend emitted by plants in response to herbivory or mechanical damage. cis-4-Hexen-1-ol is therefore used as an authentic standard in ecological studies measuring plant defense responses and insect olfaction.

Safe Handling, Storage & Stability

Personal Protective Equipment: When working with cis-4-Hexen-1-ol, wear appropriate chemical-resistant gloves (e.g., nitrile), safety glasses or goggles, and a laboratory coat. Work in a well-ventilated area or a fume hood to avoid inhalation of vapors. As a low-molecular-weight allylic alcohol, it may cause skin and eye irritation upon direct contact; avoid prolonged exposure.

Storage Conditions: Store the compound in a tightly sealed container, away from heat sources and open flames, in a cool, dry, and well-ventilated location. Protect from light to minimize photoisomerization of the cis double bond. Refrigerated storage (2–8 °C) is generally recommended for long-term stability. Keep away from strong oxidizing agents, strong acids, and strong bases that could react with either the hydroxyl group or the alkene moiety.

Stability Considerations: The cis-configured double bond can undergo slow isomerization to the trans isomer under prolonged UV exposure or in the presence of certain catalysts. Regularly verify geometric purity by GC or NMR analysis if isomeric integrity is critical to the experiment. Confirm current SDS and specification sheet for precise hazard classification and purity data before use.

Quality, Purity & Ordering Information

Aladdin Scientific supplies cis-4-Hexen-1-ol under SKU C153483. Researchers should consult the product specification sheet available on the product page for the exact purity grade, analytical data (GC purity, refractive index, specific gravity), and available pack sizes prior to ordering.

For applications requiring high geometric purity (e.g., asymmetric synthesis, sensory standards), confirm the cis/trans ratio reported in the certificate of analysis (CoA). Bulk quantities may be available upon request for industrial research or scale-up studies; contact Aladdin Scientific sales for custom quotations. Ensure that procurement records include the lot number and CoA for full traceability in regulated research environments.

Frequently asked questions

What is the difference between cis-4-Hexen-1-ol and trans-4-Hexen-1-ol?

The two compounds are geometric (cis/trans) isomers differing only in the spatial arrangement of substituents around the C4–C5 double bond. The cis (Z) isomer has both carbon chains on the same side of the double bond, resulting in distinct physicochemical properties—including boiling point, refractive index, and odor character—compared to the trans (E) isomer. In flavor and fragrance research, the two isomers typically exhibit different odor thresholds and sensory descriptors.

How should cis-4-Hexen-1-ol be stored to prevent isomerization?

Store cis-4-Hexen-1-ol in a tightly sealed, amber or opaque glass container at 2–8 °C, away from light, heat, and UV sources. Exposure to UV radiation or acidic/basic conditions can promote cis-to-trans isomerization over time. Periodically verify geometric purity by GC or ¹H NMR if the cis isomer is critical for your application.

What are the primary synthetic uses of cis-4-Hexen-1-ol in the laboratory?

cis-4-Hexen-1-ol serves as a versatile building block in organic synthesis. The primary alcohol group is readily converted to esters, halides, mesylates, or tosylates, while the cis-alkene can be subjected to epoxidation (including Sharpless asymmetric epoxidation), dihydroxylation, cross-metathesis, and hydroboration reactions. These transformations make it a useful precursor for chiral intermediates and natural product synthesis.

Is cis-4-Hexen-1-ol suitable as an analytical reference standard for plant volatile studies?

Yes. cis-4-Hexen-1-ol is a member of the green leaf volatile (GLV) family and is authentically produced by plants under biotic or mechanical stress. High-purity material with a certified cis/trans ratio is required for accurate quantification in GC-MS-based plant volatile profiling. Confirm the purity and geometric isomer ratio from the CoA before use as a reference standard.

References

1. Hatanaka, A. (1993). The biogeneration of green odour by green leaves. Phytochemistry, 34(5), 1201–1218. doi:10.1016/0031-9422(93)85502-I
2. Sharpless, K. B., & Michaelson, R. C. (1973). High stereo- and regioselectivities in the transition metal catalyzed epoxidations of homoallylic and bishomoallylic alcohols by tert-butyl hydroperoxide. Journal of the American Chemical Society, 95(18), 6136–6137. doi:10.1021/ja00849a062
3. Turlings, T. C. J., & Erb, M. (2018). Tritrophic interactions mediated by herbivore-induced plant volatiles: mechanisms, ecological relevance, and application potential. Annual Review of Entomology, 63, 433–452. doi:10.1146/annurev-ento-020117-043507

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