''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 Poaceae () or Gramineae () is a large and nearly ubiquitous family of monocotyledonous flowering plants commonly known as grasses. It includes the cereal grasses, bamboos and the grasses of natural grassland and species cultivated in lawns a ...

and leaves. It is produced in small amounts by most

plant Plants are predominantly photosynthetic eukaryotes of the kingdom Plantae. Historically, the plant kingdom encompassed all living things that were not animals, and included algae and fungi; however, all current definitions of Plantae exclu ...

s and it acts as an

attractant An attractant is any chemical that attracts an organism, e.g. i) synthetic lures; ii) aggregation and sex pheromones (intraspecific interactions); and iii) synomone (interspecific interactions) Synomone An interspecific semiochemical that is b ...

to many

predator Predation is a biological interaction where one organism, the predator, kills and eats another organism, its prey. It is one of a family of common feeding behaviours that includes parasitism and micropredation (which usually do not kill th ...

insect Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body ( head, thorax and abdomen), three ...

s. ''cis''-3-Hexen-1-ol is a very important

aroma compound An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently v ...

that is used in fruit and vegetable flavors and in

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s. The yearly production is about 30

tonne The tonne ( or ; symbol: t) is a unit of mass equal to 1000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton to distinguish it from the non-metric units of the short ton ( United State ...

s. ''cis''-3-Hexen-1-ol is an alcohol and its

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s are also important flavor and fragrance raw materials. The related

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

''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 A semiochemical, from the Greek wiktionary:σημεῖον, σημεῖον (''semeion''), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication c ...

involved in mechanisms and behaviors of attraction in diverse animals such as

insects Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, thorax and abdomen), three pairs of j ...

and

mammals Mammals () are a group of vertebrate animals constituting the class Mammalia (), characterized by the presence of mammary glands which in females produce milk for feeding (nursing) their young, a neocortex (a region of the brain), fur o ...

. However, there is no scientific evidence of its

aphrodisiac An aphrodisiac is a substance that increases sexual desire, sexual attraction, sexual pleasure, or sexual behavior. Substances range from a variety of plants, spices, foods, and synthetic chemicals. Natural aphrodisiacs like cannabis or cocai ...

effects in humans. The popular Mexican alcoholic beverage,

mezcal Mezcal (, ), sometimes spelled mescal, is a distilled alcoholic beverage made from any type of agave. The word ''mezcal'' comes from Nahuatl , which means "oven-cooked agave", from and .What is MezcalElmezcal.org Traditionally the word " ...

, is found to have enhanced concentrations of this compound when a

maguey worm Maguey worms ( es, gusano del maguey, ; ), are one of two species of edible caterpillars that infest maguey (''Agave americana'') and '' Agave tequilana'' plants. White maguey worm The white maguey worms, known as ''meocuiles'', are caterpill ...

is served in the glass.

Human odor perception

A pair of two

single-nucleotide polymorphism In genetics, a single-nucleotide polymorphism (SNP ; plural SNPs ) is a germline substitution of a single nucleotide at a specific position in the genome. Although certain definitions require the substitution to be present in a sufficiently lar ...

s, both in the gene for the

OR2J3 Olfactory receptor 2J3 is a protein that in humans is encoded by the ''OR2J3'' gene. Olfactory receptors interact with odorant molecules in the nose, to initiate a neuronal response that triggers the perception of a smell. The olfactory receptor p ...

odor receptor, strongly reduce sensitivity to this odorant.

References

External links

Pheromone database

That Worm at the Bottom of Your Mezcal Isn’t a Total Lie
{{DEFAULTSORT:Hex-1-ol, cis-3- Flavors Alkenols