Geraniol is a

monoterpenoid Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

and an alcohol. It is the primary component of

citronella oil Citronella oil Citronella oil is an essential oil obtained from the leaves and stems of different species of ''Cymbopogon'' (lemongrass). The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol, and geranio ...

and is a primary component of

rose oil Rose oil (rose otto, attar of rose, attar of roses, or rose essence) is the essential oil extracted from the petals of various types of rose. ''Rose ottos'' are extracted through steam distillation, while ''rose absolutes'' are obtained through ...

palmarosa ''Cymbopogon martinii'' is a species of grass in the genus ''Cymbopogon'' (lemongrasses) native to India and Indochina, but widely cultivated in many places for its aromatic oil. It is best known by the common name palmarosa (''palm rose'') as it ...

oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl.

Uses and occurrence

In addition to

oil, and

, it also occurs in small quantities in geranium,

lemon The lemon (''Citrus limon'') is a species of small evergreen trees in the flowering plant family Rutaceae, native to Asia, primarily Northeast India (Assam), Northern Myanmar or China. The tree's ellipsoidal yellow fruit is used for culin ...

, and many other

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

s. With a

rose A rose is either a woody perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred species and tens of thousands of cultivars. They form a group of plants that can be ...

-like scent, it is commonly used 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. It is used in flavors such as

peach The peach (''Prunus persica'') is a deciduous tree first domesticated and cultivated in Zhejiang province of Eastern China. It bears edible juicy fruits with various characteristics, most called peaches and others (the glossy-skinned, non-fu ...

raspberry The raspberry is the edible fruit of a multitude of plant species in the genus ''Rubus'' of the rose family, most of which are in the subgenus '' Idaeobatus''. The name also applies to these plants themselves. Raspberries are perennial with w ...

grapefruit The grapefruit (''Citrus'' × ''paradisi'') is a subtropical citrus tree known for its relatively large, sour to semi-sweet, somewhat bitter fruit. The interior flesh is segmented and varies in color from pale yellow to dark pink. Grapefruit is ...

, red apple,

plum A plum is a fruit of some species in ''Prunus'' subg. ''Prunus'.'' Dried plums are called prunes. History Plums may have been one of the first fruits domesticated by humans. Three of the most abundantly cultivated species are not found i ...

lime Lime commonly refers to: * Lime (fruit), a green citrus fruit * Lime (material), inorganic materials containing calcium, usually calcium oxide or calcium hydroxide * Lime (color), a color between yellow and green Lime may also refer to: Botany ...

orange Orange most often refers to: *Orange (fruit), the fruit of the tree species '' Citrus'' × ''sinensis'' ** Orange blossom, its fragrant flower *Orange (colour), from the color of an orange, occurs between red and yellow in the visible spectrum * ...

watermelon Watermelon (''Citrullus lanatus'') is a flowering plant species of the Cucurbitaceae family and the name of its edible fruit. A scrambling and trailing vine-like plant, it is a highly cultivated fruit worldwide, with more than 1,000 varieti ...

pineapple The pineapple (''Ananas comosus'') is a tropical plant with an edible fruit; it is the most economically significant plant in the family Bromeliaceae. The pineapple is indigenous to South America, where it has been cultivated for many centuri ...

, and

blueberry Blueberries are a widely distributed and widespread group of perennial flowering plants with blue or purple berries. They are classified in the section ''Cyanococcus'' within the genus ''Vaccinium''. ''Vaccinium'' also includes cranberries, bi ...

. Geraniol is produced by the

scent glands Scent gland are exocrine glands found in most mammals. They produce semi-viscous secretions which contain pheromones and other semiochemical compounds. These odor-messengers indicate information such as status, territorial marking, mood, and sexu ...

honeybee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the current cosm ...

s to mark nectar-bearing flowers and locate the entrances to their hives. It is also commonly used as an insect repellent, especially for mosquitoes. The scent of geraniol is reminiscent of, but chemically unrelated to, 2-ethoxy-3,5-hexadiene, also known as geranium taint, a wine fault resulting from fermentation of

sorbic acid Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula and the structure . It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isol ...

lactic acid bacteria Lactobacillales are an order of gram-positive, low-GC, acid-tolerant, generally nonsporulating, nonrespiring, either rod-shaped (bacilli) or spherical (cocci) bacteria that share common metabolic and physiological characteristics. These bacte ...

. Geraniol pyrophosphat is important in

biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...

of other

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...

s such as

myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from '' Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. ...

and

ocimene Ocimenes are a group of isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. α-Ocimene and the two β-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. ...

Reactions

acidic In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

solutions, geraniol is converted to the cyclic terpene α-terpineol. The alcohol group undergoes expected reactions. It can be converted to the

tosylate In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

, which is a precursor to the chloride. Geranyl chloride also arises by the

Appel reaction The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbo ...

by treating geraniol with triphenylphosphine and carbon tetrachloride. It can be hydrogenated. It can be oxidized to the aldehyde

geranial Citral is an acyclic monoterpene aldehyde, and being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the ''E''-isomer is named geranial (''trans ...

Health and safety

Geraniol is classified as D2B (Toxic materials causing other effects) using the

Workplace Hazardous Materials Information System The Workplace Hazardous Materials Information System (WHMIS; french: links=no, Système d'information sur les matières dangereuses utilisées au travail, SIMDUT) is Canada's national workplace hazard communication standard. The key elements of t ...

(WHMIS).

History

Geraniol was first isolated in pure form in 1871 by the German chemist

Oscar Jacobsen Oscar Jacobsen (1 January 1850 – 6 August 1902) was a Norwegian engineer and politician for the Liberal Party. Personal life He was born in Vågå as the son of Johanne Georgine Jørgensen and her husband Nils Lauritz Severin Jacobsen. He h ...

(1840–1889). Using

distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...

, Jacobsen obtained geraniol from an essential oil which was obtained from geranium grass ('' Andropogon schoenanthus'') and which was produced in India. The chemical structure of geraniol was determined in 1919 by the French chemist Albert Verley (1867–1959). The chemical structure of geraniol appears on p. 70.

References

External links