Rhodinol

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Rhodinol
Rhodinol.png
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Names
Preferred IUPAC name
(3S)-3,7-Dimethyloct-7-en-1-ol
Other names
α-Citronellol, 3,7-Dimethyl-(6- or 7-)octen-1-ol, 3,7-Dimethyl-7-octen-1-ol, 1-Citronellol
Identifiers
  • 6812-78-8 Yes check.svgY
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.977 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-887-4
  • 205-473-9
PubChem CID
UNII
  • C[C@H](CCO)CCCC(C)=C
Properties
C10H20O
Molar mass 156.269 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H315, H317, H318, H319, H411
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Rhodinol is the chemical compound 3,7-dimethyloct-7-en-1-ol. As the (3S) isomer it is CAS 6812-78-8, and as the racemate it is CAS 141-25-3.

In the field of perfumery materials, the term may refer to L-citronellol, to mixtures comprising mostly L- or racemic citronellol and geraniol, or to mixtures comprising mostly racemic 3,7-dimethyloct-7-en-1-ol and racemic citronellol.

Two example synthetic Rhodinol products are Rhodinol 70, a racemic mixture comprising 40-60% 3,7-dimethyloct-7-en-1-ol and 40-60% citronellol, and Sigma-Aldrich Rhodinol, which consists of L-citronellol and geraniol.

Rhodinol is also provided in perfumery in natural grades as materials extracted from geranium or citronella, comprising principally citronellol and geraniol.

Rhodinol products are used in cosmetics and perfumery to impart flowery odors, particularly but not limited to being a component of rosy odor. [1]

3,7-Dimethyloct-7-en-1-ol does not appear substantively in nature. [2]

See also

Related Research Articles

Perfume Mixture of fragrant substances, usually in liquid form, used to give agreeable scent to objects, air or living creatures

Perfume 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. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory."

A CAS Registry Number, also referred to as CAS RN or informally CAS Number, is a unique numerical identifier assigned by the Chemical Abstracts Service (CAS) to every chemical substance described in the open scientific literature. Currently it includes all substances described from 1957 through the present, plus some substances from as far back as the early 1800s. It includes organic and inorganic compounds, minerals, isotopes, alloys, mixtures, and nonstructurable materials. CAS RNs are generally serial numbers, so they do not contain any information about the structures themselves the way SMILES and InChI strings do.

Musk Class of aromatic substances used of perfumes

Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. Musk was a name originally given to a substance with a strong odor obtained from a gland of the musk deer. The substance has been used as a popular perfume fixative since ancient times and is one of the most expensive animal products in the world. The name originates from the Late Greek μόσχος 'moskhos', from Persian 'mushk', similar to Sanskrit मुष्क muṣka ("testicle"), derived from Proto-Indo-European noun múh₂s meaning "mouse". The deer gland was thought to resemble a scrotum. It is applied to various plants and animals of similar smell and has come to encompass a wide variety of aromatic substances with similar odors, despite their often differing chemical structures and molecular shapes.

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 geraniol. These chemicals find extensive use in soap, candles and incense, perfumery, cosmetic, and flavouring industries throughout the world. Citronella oil is also a plant-based insect repellent and has been registered for this use in the United States since 1948. The United States Environmental Protection Agency considers oil of citronella as a biopesticide with a non-toxic mode of action.

Geraniol a monoterpenoid and alcohol that is the primary component of citronella oil

Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa 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 derived from geraniol is called geranyl.

Citral Chemical compound

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-Citral) or Citral A. The Z-isomer is named Neral (cis-Citral) or Citral B. These enantiomers occur as a mixture, not necessarily racemic; e.g. in essential oil of Australian ginger, the Neral to Geranial ratio is 0.61.

Limonene Chemical compound

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the oil of citrus fruit peels. The D-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common L-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

Rose oil Essential oil

Rose oil 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 solvent extraction, the absolute being used more commonly in perfumery. The production technique originated in Persia. Even with their high price and the advent of organic synthesis, rose oils are still perhaps the most widely used essential oil in perfumery.

Myrcene Chemical compound

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Citronellol Pair of enantiomers

Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer. (−)-Citronellol is found in the oils of rose (18–55%) and Pelargonium geraniums.

Farnesol Chemical compound

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils.

Prenol Chemical compound

Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenoids. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used occasionally in perfumery.

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 functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

C<sub>5</sub>H<sub>8</sub> Index of chemical compounds with the same molecular formula

The molecular formula C5H8 may refer to any of the following hydrocarbons:

OR2M7

Olfactory receptor 2M7 is a protein that in humans is encoded by the OR2M7 gene.

Rose oxide Chemical compound

Rose oxide is a fragrance chemical found in roses and rose oil. It also contributes to the flavor of some fruits, such as lychee, and wines, such as Gewürztraminer.

Lilial Chemical compound

Lilial is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders, often under the name butylphenyl methylpropional. It is a synthetic aromatic aldehyde.

Galaxolide Chemical compound

Galaxolide is a synthetic musk with a clean sweet musky floral woody odor used in fragrances. It is one of the musk components that perfume and cologne manufacturers use to add a musk odor to their products. Galaxolide was first synthesized in 1965, and used in the late 1960s in some fabric softeners and detergents. High concentrations were also incorporated in fine fragrances.

4-Methylcyclohexanemethanol Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

Civet, also known as civet musk and civet oil, is the glandular secretion produced by both sexes of Viverridae species.

References

  1. Rhodinol The Good Scents Company
  2. The Citronellol Problem and the Isolation of α-Citronellol Journal of the American Chemical Society