Rose oil

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Rose (Rosa damascena) essential oil in clear glass vial RoseEssentialOil.png
Rose (Rosa damascena) essential oil in clear glass vial

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, [1] while rose absolutes [2] are obtained through solvent extraction, the absolute being used more commonly in perfumery. The production technique originated in Greater Iran. [3] [4] Even with their high price and the advent of organic synthesis, rose oils are still perhaps the most widely used essential oil in perfumery.

Contents

R. damascena and R. centifolia

Two major species of rose are cultivated for the production of rose oil: [5]

Rosa damascena composition

Composition of rose oil and headspace vary, but the Rose international standard survey of 2003–2020 lists three components as the major components with a specific range specified in ISO 9842:2003. [6]

Major rose components

Minor rose components

Heneicosane, eicosane, docosane, tricosane, tetracosane, pentacosane, hexacosane, heptacosane, nonacosane, dodecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nerol, linalool, phenyl ethyl alcohol, farnesol, α-pinene, β-pinene, α-terpinene, limonene, p-cymene, camphene, β-caryophyllene, neral, geranyl acetate, neryl acetate, eugenol, methyl eugenol, benzaldehyde, benzyl alcohol, octane and tetradecanol. [7]

Key rose components

Beta-damascenone's presence is considered as the marker for the quality of rose oil. Even though these compounds usually exist in less than 1% quantity of rose oil, they make up for slightly more than 90% of the odor content due to their low odor detection thresholds. [8]

Rosa centifolia composition

Rosa centifolia does not have a rose oil because of the delicate nature of its petals. The Rosa centifolia absolute is composed of more than 50% phenylethyl alcohol and the rest of the composition resembles a Rosa damascena. [9]

Production

Rose oil factory in Bulgaria BASA-2072K-1-321-17-Rose oil factory, Bulgaria.JPG
Rose oil factory in Bulgaria
Rose-picking in the Rose Valley near the town of Kazanlak in Bulgaria, 1870s, engraving by Austro-Hungarian traveller Felix Philipp Kanitz Rose-picking in Bulgaria 1870ies.jpg
Rose-picking in the Rose Valley near the town of Kazanlak in Bulgaria, 1870s, engraving by Austro-Hungarian traveller Felix Philipp Kanitz

Due to the labor-intensive production process and the low content of oil in the rose blooms, rose oil commands a very high price. Harvesting of flowers is done by hand in the morning before sunrise, and the material is distilled the same day.

There are three main methods of extracting the oil from the plant material:

Distillation

In the first part of the two-stage process of distillation, large stills – traditionally of copper – are filled with roses and water. The still is fired for 60–105 minutes. The vaporized water and rose oil exit the still and enter a condensing apparatus and are then collected in a flask. This distillation yields a very concentrated oil, direct oil, which makes up about 20% of the final product of the whole process. The water which condenses along with the oil is drained off and redistilled, cohobation, in order to obtain the water-soluble fractions of the rose oil such as phenethyl alcohol which are a vital component of the aroma and which make up the large bulk, 80%, of the oil. The two oils are combined and make the final rose attar.

Rose attar is mobile in room temperature and is usually clear, light yellow in color. It will form white crystals at normal room temperature which disappear when the oil is gently warmed. It will tend to become more viscous at lower temperatures due to this crystallization of some of its components.

The essence has a very strong odor, but is pleasant when diluted and used for perfume. Attar of roses was once made in India, Persia, Syria, and the Ottoman Empire. The Rose Valley in Bulgaria, near the town of Kazanlak, is among the major producers of attar of roses in the world. [10] In India, Kannauj is an important city of fabrication of rose attar, Kannauj is nicknamed "The Grasse of the East" or "The Grasse of the Orient". Grasse (in France) is an important city of fabrication of rose fragrance.

Due to the heat required for distillation, some of the compounds extracted from the rose denature or break down chemically. As such, rose attar does not smell very similar to "fresh" roses.

The hydrosol portion of the distillate is known as rosewater . This inexpensive by-product is used widely as a food flavoring as well as in skin care.

Solvent extraction

In the solvent extraction method, the flowers are agitated in a vat with a solvent such as hexane, which draws out the aroma compounds as well as other soluble substances such as wax and pigments. The extract is subjected to vacuum processing which removes the solvent for re-use. The remaining waxy mass is known as a concrete . The concrete is then mixed with alcohol which dissolves the aromatic constituents, leaving behind the wax and other substances. The alcohol is low-pressure evaporated, leaving behind the finished absolute. The absolute may be further processed to remove any impurities that are still present from the solvent extraction.

Rose absolute is a deep reddish brown with no crystals. Due to the low temperatures in this process, the absolute may be more faithful to the scent of the fresh rose than the otto.

Carbon dioxide extraction

A third process, supercritical carbon dioxide extraction, combines the best aspects of the other two methods. When carbon dioxide is put under at least 72.9 atm (73.9 bar) of pressure and at a temperature of at least 31.1 °C (88.0 °F) (the critical point), it becomes a supercritical fluid with the permeation properties of a gas and the solvation properties of a liquid. (Under normal pressure CO
2
changes directly from a solid to a gas in a process known as sublimation.) The supercritical fluid CO
2
extracts the aromatics from the plant material.

Like solvent extraction, the CO
2
extraction takes place at a low temperature, extracts a wide range of compounds rendering an essence more faithful to the original, and leaves the aromatics unaltered by heat. Because CO
2
is gas at normal atmospheric pressure, it leaves no trace of itself in the final product. The equipment for CO
2
extraction is expensive, which is reflected in the price of the essential oils obtained from the process.

Adulteration

It takes a large amount of rose petals to distill a small amount of essential oil. Depending on extraction method and plant species, the typical yield can be approximately 1:3,000. [11] To mitigate the cost, most dealers cut rose oil with Citronellol, Geraniol, Geranium or Palmarosa ( Cymbopogon martinii ) essential oils, both of which are rich in Geraniol, the main constituent of rose oil. Some of these "rose oils" are up to 90% geranium or palmarosa to 10% rose. This is referred to as extending the rose fragrance. This may be done to compensate for chemotype, e.g. Bulgarian distilled rose oil is naturally low in phenylethanol, and Ukrainian or Russian rose oil is naturally high in phenylethanol. Pure rose oil should not be used directly on the skin, as it can cause allergic reactions such as red skin and spots.[ medical citation needed ]

Bulgarian rose oil

Bulgarian rose oil is generally characterized by the following qualities: [1]

Related Research Articles

<span class="mw-page-title-main">Rose</span> Genus of plants

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 erect shrubs, climbing, or trailing, with stems that are often armed with sharp prickles. Their flowers vary in size and shape and are usually large and showy, in colours ranging from white through yellows and reds. Most species are native to Asia, with smaller numbers native to Europe, North America, and northwestern Africa. Species, cultivars and hybrids are all widely grown for their beauty and often are fragrant. Roses have acquired cultural significance in many societies. Rose plants range in size from compact, miniature roses, to climbers that can reach seven meters in height. Different species hybridize easily, and this has been used in the development of the wide range of garden roses.

<span class="mw-page-title-main">Rose water</span> Rose-flavored water

Rose water is a flavoured water made by steeping rose petals in water. It is the hydrosol portion of the distillate of rose petals, a by-product of the production of rose oil for use in perfume. Rose water is also used to flavour food, as a component in some cosmetic and medical preparations, and for religious purposes throughout Eurasia.

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. Perfumes can be defined as substances that emit and diffuse a pleasant and fragrant odor. They consist of manmade mixtures of aromatic chemicals and essential oils. 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."

<span class="mw-page-title-main">Essential oil</span> Hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does not mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism.

<span class="mw-page-title-main">Absolute (perfumery)</span>

Used in perfumery and aromatherapy, absolutes are similar to essential oils. They are concentrated, highly aromatic, oily mixtures extracted from plants. Whereas essential oils are produced by distillation, boiling, or pressing, absolutes are produced through solvent extraction, or more traditionally, through enfleurage.

<span class="mw-page-title-main">Citronella oil</span> Fragrant essential oil derived from lemongrass

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.

Enfleurage is a process that uses odorless fats that are solid at room temperature to capture the fragrant compounds, such as volatile oils, produced by plants. The process can be "cold" enfleurage or "hot" enfleurage.

<span class="mw-page-title-main">Geraniol</span> 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 and 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.

<span class="mw-page-title-main">Steam distillation</span> Method of separation in organic chemistry

Steam distillation is a separation process that consists of distilling water together with other volatile and non-volatile components. The steam from the boiling water carries the vapor of the volatiles to a condenser; both are cooled and return to the liquid or solid state, while the non-volatile residues remain behind in the boiling container.

Nutmeg oil is a volatile essential oil from nutmeg. The oil is colorless or light yellow and smells and tastes of nutmeg. It contains numerous components of interest to the oleochemical industry. The essential oil consists of approximately 90% terpene hydrocarbons. Prominent components are sabinene, α-pinene, β-pinene, and limonene. A major oxygen-containing component is terpinen-4-ol. The oil also contains small amounts of various phenolic compounds and aromatic ethers, e.g. myristicin, elemicin, safrole, and methyl eugenol. The phenolic fraction is considered main contributor to the characteristic nutmeg odor. However, in spite of the low oil content, the characteristic composition of nutmeg oil makes it a valuable product for food, cosmetic and pharmaceutical industries. Therefore, an improved process for its extraction would be of industrial interest.

Supercritical fluid extraction (SFE) is the process of separating one component (the extractant) from another (the matrix) using supercritical fluids as the extracting solvent. Extraction is usually from a solid matrix, but can also be from liquids. SFE can be used as a sample preparation step for analytical purposes, or on a larger scale to either strip unwanted material from a product (e.g. decaffeination) or collect a desired product (e.g. essential oils). These essential oils can include limonene and other straight solvents. Carbon dioxide (CO2) is the most used supercritical fluid, sometimes modified by co-solvents such as ethanol or methanol. Extraction conditions for supercritical carbon dioxide are above the critical temperature of 31 °C and critical pressure of 74 bar. Addition of modifiers may slightly alter this. The discussion below will mainly refer to extraction with CO2, except where specified.

<span class="mw-page-title-main">Neroli</span> Essential oil of the bitter orange blossom

Neroli oil is an essential oil produced from the blossom of the bitter orange tree. Its scent is sweet, honeyed and somewhat metallic with green and spicy facets. Orange blossom is also extracted from the same blossom and both extracts are extensively used in perfumery. Orange blossom can be described as smelling sweeter, warmer and more floral than neroli. The difference between how neroli and orange blossom smell and why they are referred to with different names, is a result of the process of extraction that is used to obtain the oil from the blooms. Neroli is extracted by steam distillation and orange blossom is extracted via a process of enfleurage or solvent extraction.

<span class="mw-page-title-main">Myrcene</span> Chemical compound

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. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.

<span class="mw-page-title-main">Citronellol</span> 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 widespread, but particularly abundant in the oils of rose (18–55%) and Pelargonium geraniums.

<span class="mw-page-title-main">Nerol</span> Chemical compound

Nerol is a monoterpenoid alcohol found in many essential oils such as lemongrass and hops. It was originally isolated from neroli oil, hence its name. This colourless liquid is used in perfumery. Like geraniol, nerol has a sweet rose odor but it is considered to be fresher. Esters and related derivatives of nerol are referred to as neryl, e.g., neryl acetate.

<i>Rosa <span style="font-style:normal;">×</span> damascena</i> Species of plant in the genus Rosa

Rosa × damascena, more commonly known as the Damask rose, or sometimes as the Iranian Rose, Bulgarian rose, Arab rose, Ispahan rose and Castile rose, is a rose hybrid, derived from Rosa gallica and Rosa moschata. DNA analysis has shown that a third species, Rosa fedtschenkoana, has made some genetic contributions to the Damask rose.

<span class="mw-page-title-main">Fragrance extraction</span> Separation process of aromatic compounds from raw materials

Fragrance extraction refers to the separation process of aromatic compounds from raw materials, using methods such as distillation, solvent extraction, expression, sieving, or enfleurage. The results of the extracts are either essential oils, absolutes, concretes, or butters, depending on the amount of waxes in the extracted product.

<span class="mw-page-title-main">Types of plant oils</span>

Plant oils or vegetable oils are oils derived from plant sources, as opposed to animal fats or petroleum. There are three primary types of plant oil, differing both the means of extracting the relevant parts of the plant, and in the nature of the resulting oil:

  1. Vegetable fats and oils were historically extracted by putting part of the plant under pressure, squeezing out the oil.
  2. Macerated oils consist of a base oil to which parts of plants are added.
  3. Essential oils are composed of volatile aromatic compounds, extracted from plants by distillation.
<span class="mw-page-title-main">Attar</span> Types of essential oils

Attar, also known as ittar, is an essential oil derived from botanical or other natural sources. Most commonly these oils are extracted via hydrodistillation or steam distillation. The Persian physician Ibn Sina was the first to derive the attar of flowers from distillation. Attar can also be expressed by chemical means but generally natural perfumes which qualify as attars are distilled with water. The oils are generally distilled into a wood base such as sandalwood and then aged. The aging period can last from one to ten years depending on the botanicals used and the results desired. Technically attars are distillates of flowers, herbs, spices and other natural materials such as baked soil over sandalwood oil/liquid paraffins using hydrodistillation technique involving a still and receiving vessel. These techniques are still in use at Kannauj in India.

References

  1. 1 2 Antonova, Daniela V.; Medarska, Yana N.; Stoyanova, Albena St.; Nenov, Nenko St.; Slavov, Anton M.; Antonov, Liudmil M. (4 March 2021). "Chemical profile and sensory evaluation of Bulgarian rose ( Rosa damascena Mill.) aroma products, isolated by different techniques". Journal of Essential Oil Research. 33 (2): 171–181. doi:10.1080/10412905.2020.1839583. S2CID   230534578.
  2. Nedeltcheva-Antonova D, Stoicheva P, Antonov L (2017). "Chemical profiling of Bulgarian rose absolute (Rosa damascena Mill.) using gas chromatography–mass spectrometry and trimethylsilyl derivatives". Industrial Crops and Products. 108: 36–43. doi:10.1016/j.indcrop.2017.06.007.
  3. Nikbakht, A.; Kafi, M. (June 2008). "A study on the relationships between Iranian people and Damask rose (Rosa damascena) and its therapeutic and healing properties". Acta Horticulturae (790): 251–254. doi:10.17660/ActaHortic.2008.790.36.
  4. Mahboubi, Mohaddese (January 2016). "Rosa damascena as holy ancient herb with novel applications". Journal of Traditional and Complementary Medicine. 6 (1): 10–16. doi:10.1016/j.jtcme.2015.09.005. PMC   4737971 . PMID   26870673.
  5. Hass, Nancy (24 September 2015). "Francis Kurkdjian and Fabien Ducher, Changing History in a Bottle". The New York Times.
  6. "Iso 9842:2003".
  7. Khan, Ikhlas A.; Abourashed, Ehab A. (2010). Leung's Encyclopedia of Common Natural Ingredients: Used in Food, Drugs and Cosmetics. Hoboken, NJ: Wiley. p. 208. ISBN   9780471467434.
  8. Leffingwell, John C. (1999). "Rose (Rosa damascena)". Aroma from Carotenoids. Leffingwell & Associates. Retrieved 2006-06-08.
  9. Boskabady, Mohammad Hossein; Shafei, Mohammad Naser; Saberi, Zahra; Amini, Somayeh (July 2011). "Pharmacological effects of rosa damascena". Iranian Journal of Basic Medical Sciences. 14 (4): 295–307. PMC   3586833 . PMID   23493250.
  10. This article incorporates text from a publication now in the public domain :  Wood, James, ed. (1907). The Nuttall Encyclopædia . London and New York: Frederick Warne.{{cite encyclopedia}}: Missing or empty |title= (help)
  11. Parry, Ernest John (1899). The Chemistry of Essential Oils and Artificial Perfumes: Illustrated with Engravings. London: Scott, Greenwood & Company. p.  288.