cis-3-Hexen-1-ol does not have a specific molecular target in the context of pharmacology; rather, it functions as a plant metabolite, insect attractant, and fragrance. In biological systems, it is produced by plants via the lipoxygenase pathway as a volatile organic compound released in response to mechanical damage or herbivory. It serves as a signaling molecule in plant-insect interactions, attracting natural enemies of herbivores.

In vitro, cis-3-Hexen-1-ol has been studied for its effects on various biological systems. It has been reported to exhibit antimicrobial activity against certain foodborne pathogens. As a flavor and fragrance compound, its sensory properties are evaluated using organoleptic testing and gas chromatography-olfactometry. The compound's stability and reactivity in different matrices are assessed through standard chemical analysis methods including GC-MS and HPLC.

In vivo, cis-3-Hexen-1-ol has been studied in animal models for its effects on behavior and physiology. It has been reported to act as an insect attractant in ecological studies. In mammals, the compound is metabolized and excreted primarily via the urine. The compound is generally recognized as safe (GRAS) for use as a food additive and flavoring agent by regulatory authorities.

In vitro enzyme/receptor binding assays for cis-3-Hexen-1-ol are not typically performed as the compound is not a drug targeting specific enzymes or receptors. However, binding studies with odorant receptors in olfactory sensory neurons have been conducted using calcium imaging or electrophysiological recordings to characterize its interaction with olfactory receptors. These assays help understand the molecular basis of its characteristic "green" odor perception.

In vitro cellular studies with cis-3-Hexen-1-ol are limited due to its primary use as a flavor and fragrance compound. However, cytotoxicity assays (e.g., MTT, LDH release) have been performed in various cell lines to evaluate its safety profile. The compound's effects on cell membrane integrity and metabolic activity are assessed at concentrations relevant to its use in food and cosmetic applications. Standard cell culture protocols apply with appropriate solvent controls.

In vivo animal experiments for cis-3-Hexen-1-ol are primarily conducted in the context of toxicology and safety assessment. Standard OECD guidelines for acute oral toxicity, skin irritation, and eye irritation are followed using rodent models. The compound is administered via oral gavage, dermal application, or inhalation, and animals are monitored for adverse effects. Ecotoxicological studies in aquatic organisms are also performed to assess environmental impact.

Pharmacokinetic properties of cis-3-Hexen-1-ol include rapid absorption following oral or inhalation exposure, extensive metabolism, and elimination primarily via urine. The compound has a density of 0.848 g/mL at 25°C and boiling point of 156°C. It is soluble in alcohol, propylene glycol, and most fixed oils, and very slightly soluble in water. It has a flash point of 44°C and should be stored away from heat and ignition sources.

Toxicity Summary
Identification and Uses: 3-Hexenol is a colorless liquid. It has a strong, freshly cut grass scent and a fresh, green fruit aroma. Many plants release 3-hexenol into the air, including grass, clover, alfalfa, grapes, onions, peaches, and oak. Almost all green parts of plants contain 3-hexenol. It has been reported to be present in many essential oils and fruit juices, and is also a component of tobacco smoke. 3-Hexenol is used as a flavoring agent in perfumes, household cleaners, and food flavorings. Human Exposure and Toxicity: Tested at a concentration of 4% in petrolatum solution, 3-hexenol did not cause human irritation in a 48-hour closed patch test. Odorization of inert gases can be used to alert workers in confined spaces. A psychophysical study investigated the potential of 3-hexenol as a potential odorizer for argon. The detection threshold for 3-hexenol in argon is 19 ppb. Regardless of the presence of hepatic enzyme metabolism, 3-hexenol did not cause a statistically significant increase in the frequency of chromosomal aberrations in human lymphocytes. Animal studies: The oral LD50 of 3-hexenol in rats and mice was 7-10 g/kg, and the intraperitoneal LD50 was 0.4-0.6 g/kg. No effects were observed at concentrations of 310 ppm and 1250 ppm, but in males at the 5000 ppm concentration group, compared to the control group, water intake was reduced, relative kidney weight was increased, and urine concentration was higher within 2 hours after drinking. In females, the only finding was transient anemia at this dose. In another study, applying full concentrations of 3-hexenol to rabbit skin for 24 hours did not cause irritation. In rats, the effects of inhaling a green odor (a mixture of trans-2-hexenal and 3-hexenol) on stress-related neuronal activation in the forebrain region induced by acute and repetitive stress were investigated by analyzing Fos proteins. The green odor inhibited stress-induced corticosterone response, weight loss, and adrenal hypertrophy. In another study, reproductive toxicity was evaluated in rats administered orally at doses of 100, 300, and 1000 mg/kg/day. Based on the results, the no-observed-adverse-effect level (NOAEL) for overall toxicity in both male and female rats was determined to be 1000 mg/kg/day, the highest dose level tested. This study evaluated the potential mutagenicity of 3-hexenol at the thymidine kinase (TK+/-) locus in the L5178Y mouse lymphoma cell line. The results showed that 3-hexenol did not cause a significant increase in the mutation frequency at the TK+/- locus in L5178Y cells and was therefore considered non-mutagenic under the conditions of this study.

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Non-human toxicity values
Rabbit dermal LD50 >5 g/kg
Rat oral LD50 4.7 g/kg
Rat intraperitoneal LD50 600 mg/kg
Mouse oral LD50 7000 mg/kg
Mouse intraperitoneal LD50 400 mg/kg
Toxicological data indicate that cis-3-Hexen-1-ol has low acute toxicity. The compound is generally recognized as safe (GRAS) for use as a flavoring agent. Skin and eye irritation studies show that it is mildly irritating at high concentrations. The oral LD50 in rats is reported to be >5 g/kg. Inhalation studies have shown low toxicity at relevant exposure levels. Standard safety precautions should be followed when handling the compound.

[1]. Genetic variation in the odorant receptor OR2J3 is associated with the ability to detect the "grassy" smelling odor, cis-3-hexen-1-ol. Chem Senses. 2012 Sep;37(7):585-93.

[2]. Spatial differences in (Z)-3-hexen-1-ol production preferentially reduces Spodoptera litura larva attack on the young leaves of Nicotiana benthamiana. Plant Sci. 2016 Nov;252:367-373.

(Z)-Hex-3-en-1-ol is a hex-3-en-1-ol with a Z-configuration of double bonds. Also known as leaf alcohol, it is a substance released by green plants when subjected to mechanical damage. It is used as a flavoring agent in tea. In addition, it has functions as an insect attractant, a plant metabolite, and a flavoring agent. Cis-3-hexen-1-ol has been reported to exist in tea plants (Camellia sinensis), perilla (Perilla frutescens), and several other organisms with relevant data. Cis-3-hexen-1-ol is a metabolite found or produced in Saccharomyces cerevisiae.
cis-3-Hexen-1-ol is also known as (Z)-hex-3-en-1-ol, leaf alcohol, and (3Z)-3-Hexen-1-ol. It has FEMA number 2563 and is approved for use as a food additive in many countries. The compound is found naturally in various plants including Camellia sinensis (tea), Perilla frutescens, and other organisms. It has a role as an insect attractant, plant metabolite, and fragrance. Storage should be in a cool, dry place away from light and oxidizing agents.

C6H12O

100.15888

100.088

928-96-1

5281167

Colorless to off-white liquid

0.848

156-157 ºC

-60ºC

44 ºC

1.0±0.6 mmHg at 25°C

1.438-1.441

1.61

1

1

3

7

48.1

0

C(/CCO)=C/CC

UFLHIIWVXFIJGU-ARJAWSKDSA-N

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3-

(Z)-hex-3-en-1-ol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~998.40 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (24.96 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (24.96 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (24.96 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)