View source for Rose oil

{{Short description|Essential oil extracted from rose petals}}
{{more citations needed|date=June 2023}}
[[Image:RoseEssentialOil.png|250px|thumb|right|Rose (''Rosa damascena'') essential oil in clear glass vial]]
'''Rose oil''' ('''rose otto''', '''attar of rose''', '''attar of roses''', or '''rose essence''') is an [[essential oil]] that is extracted from the [[petal]]s of various types of [[rose]]. ''Rose ottos'' are extracted through [[steam distillation]],<ref name="Nedeltcheva2021">{{cite journal |last1=Antonova |first1=Daniela V. |last2=Medarska |first2=Yana N. |last3=Stoyanova |first3=Albena St. |last4=Nenov |first4=Nenko St. |last5=Slavov |first5=Anton M. |last6=Antonov |first6=Liudmil M. |title=Chemical profile and sensory evaluation of Bulgarian rose ( Rosa damascena Mill.) aroma products, isolated by different techniques |journal=Journal of Essential Oil Research |date=4 March 2021 |volume=33 |issue=2 |pages=171–181 |doi=10.1080/10412905.2020.1839583 |s2cid=230534578 |url=https://figshare.com/articles/journal_contribution/13353272 |url-access=subscription }}</ref> while ''rose absolutes''<ref>{{cite journal | vauthors = Nedeltcheva-Antonova D, Stoicheva P, Antonov L| title = Chemical profiling of Bulgarian rose absolute (Rosa damascena Mill.) using gas chromatography–mass spectrometry and trimethylsilyl derivatives| journal = Industrial Crops and Products | volume = 108 | pages = 36–43 | date = 2017 | doi = 10.1016/j.indcrop.2017.06.007 }}</ref> are obtained through [[solvent extraction]], the [[absolute (perfumery)|absolute]] being used more commonly in [[perfumery]]. The production technique originated in [[Greater Iran]].<ref>{{cite journal |last1=Nikbakht |first1=A. |last2=Kafi |first2=M. |title=A study on the relationships between Iranian people and Damask rose (Rosa damascena) and its therapeutic and healing properties |journal=Acta Horticulturae |date=June 2008 |issue=790 |pages=251–254 |doi=10.17660/ActaHortic.2008.790.36 }}</ref><ref>{{cite journal |last1=Mahboubi |first1=Mohaddese |title=Rosa damascena as holy ancient herb with novel applications |journal=Journal of Traditional and Complementary Medicine |date=January 2016 |volume=6 |issue=1 |pages=10–16 |doi=10.1016/j.jtcme.2015.09.005 |pmid=26870673 |pmc=4737971 }}</ref> Even with their high price and the advent of [[organic synthesis]], rose oils are still perhaps the most widely used essential oil in perfumery.

==''R. damascena'' and ''R. centifolia''==
Two major species of rose are cultivated for the production of rose oil:<ref>{{cite news |last1=Hass |first1=Nancy |title=Francis Kurkdjian and Fabien Ducher, Changing History in a Bottle |url=https://www.nytimes.com/2015/09/24/t-magazine/francis-kurkdijan-fabien-ducher-rose.html |work=The New York Times |date=24 September 2015 }}</ref>
* ''[[Rosa damascena]]'' production today is dominated by 3 producers account for over 70% of the Rose oil market share:
** [[Bulgaria]], sold as "Bulgarian Rose"
** [[Turkey]], sold as "Turkish Rose"
** [[Saudi Arabia]], sold as "Taif Rose"
** It is also grown on a smaller scale in Afghanistan, Armenia, Azerbaijan, Bosnia, Croatia, Cyprus, Ethiopia, Georgia, Greece, Jordan, Lebanon, India, Iran, Iraq, Israel, Moldova, North Macedonia, Oman, Serbia, Syria, Tajikistan, Turkmenistan, Pakistan, Romania, Russia, Ukraine, United Arab Emirates and Yemen.
* ''[[Rosa centifolia]]'', the cabbage rose, which is more commonly grown in Morocco, Egypt and France.

===''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.<ref>{{cite web | url=https://www.iso.org/standard/28611.html | title=Iso 9842:2003 }}</ref>

====Major rose components====
* [[Citronellol]] 20–34%
* [[Geraniol]] 15–22%
* [[Nonadecane]] 8–15%

====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]], [[Citral|neral]],
[[geranyl acetate]], [[neryl acetate]], [[eugenol]], [[methyl eugenol]], [[benzaldehyde]], [[benzyl alcohol]], [[octane]] and  [[tetradecanol]].<ref name="KhanAbourashed2011">{{cite book|last1=Khan|first1=Ikhlas A. |last2=Abourashed|first2=Ehab A. |title=Leung's Encyclopedia of Common Natural Ingredients: Used in Food, Drugs and Cosmetics|url=https://books.google.com/books?id=kIP2Lf9H4dkC&pg=PA208|year=2010|publisher=Wiley|location=Hoboken, NJ|isbn= 9780471467434|page=208}}</ref>

====Key rose components====
* [[β-damascenone]] (0.01–1.85%)
* [[beta-damascone|β-damascone]] (under 1%)
* [[damascone|other damascones]] (under 1%)
* [[beta-ionone]] (under 1%)
* [[rose oxide]] (under 1%)

[[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 threshold]]s.<ref>{{cite web|author=Leffingwell, John C.|year=1999|title=Rose (Rosa damascena)|work=Aroma from Carotenoids|publisher=Leffingwell & Associates|url=http://www.leffingwell.com/rose.htm|access-date=2006-06-08}}</ref>

=== ''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''.<ref>{{cite journal |last1=Boskabady |first1=Mohammad Hossein |last2=Shafei |first2=Mohammad Naser |last3=Saberi |first3=Zahra |last4=Amini |first4=Somayeh |title=Pharmacological effects of rosa damascena |journal=Iranian Journal of Basic Medical Sciences |date=July 2011 |volume=14 |issue=4 |pages=295–307 |pmid=23493250 |pmc=3586833 }}</ref>

== Production ==
{{main|Extraction (fragrance)}}
[[File:BASA-2072K-1-321-17-Rose oil factory, Bulgaria.JPG|thumb|left|upright|Rose oil factory in Bulgaria]]
[[Image:Rose-picking in Bulgaria 1870ies.jpg|upright|thumb|right|Rose-picking in the [[Rose Valley, Bulgaria|Rose Valley]] near the town of [[Kazanlak]] in [[Bulgaria]], 1870s, engraving by [[Austria-Hungary|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:

* [[Steam distillation]], which produces an [[essential oil]] called ''rose otto'' or ''attar of roses''.
* [[Solvent extraction]], which results in an [[absolute (perfumery)|absolute]] called ''rose absolute''.
* [[Supercritical carbon dioxide]] extraction, yielding a [[concrete (perfumery)|concrete]] that may be marketed as a ''concrete'', ''absolute'' or ''{{chem|C|O|2}} extract''.

===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, Bulgaria|Rose Valley]] in Bulgaria, near the town of [[Kazanlak]], is among the major producers of attar of roses in the world.<ref>{{Nuttall}}</ref>
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 [[Denaturation (biochemistry)|denature]] or break down chemically. As such, rose attar does not smell very similar to "fresh" roses.

The [[Herbal distillate|hydrosol]] portion of the distillate is known as ''[[Rose water|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 compound]]s as well as other soluble substances such as [[wax]] and [[pigment]]s. The extract is subjected to vacuum processing which removes the solvent for re-use. The remaining waxy mass is known as a ''[[concrete (extraction)|concrete]]''. The concrete is then mixed with [[Alcohol (chemistry)|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 {{convert|72.9|atm|bar|abbr=on}} of pressure and at a temperature of at least {{convert|31.1|C|F}} (the [[Critical point (thermodynamics)|critical point]]), it becomes a supercritical fluid with the permeation properties of a gas and the solvation properties of a liquid. (Under normal pressure {{chem|C|O|2}} changes directly from a solid to a gas in a process known as [[Sublimation (chemistry)|sublimation]].) The supercritical fluid {{chem|C|O|2}} extracts the aromatics from the plant material.

Like solvent extraction, the {{chem|C|O|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 {{chem|C|O|2}} is gas at normal [[atmospheric pressure]], it leaves no trace of itself in the final product. The equipment for {{chem|C|O|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 [[petal]]s to distill a small amount of essential oil. Depending on extraction method and plant species, the typical yield can be approximately 1:3,000.<ref name="Parry1899">{{cite book|last=Parry|first=Ernest John|title=The Chemistry of Essential Oils and Artificial Perfumes: Illustrated with Engravings|url=https://archive.org/details/b28059979|year=1899|publisher=Scott, Greenwood & Company|location=London|page=[https://archive.org/details/b28059979/page/n299 288]}}</ref> To mitigate the cost, most dealers cut rose oil with [[Citronellol]], [[Geraniol]], [[Pelargonium|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.{{medcn|date=August 2014}}

=== Bulgarian rose oil ===
Bulgarian rose oil is generally characterized by the following qualities:<ref name="Nedeltcheva2021"/>

* It differs to other rose oils in the quantitative content of its ingredients. About 283 components have been identified in the composition of Bulgarian rose oil. They are divided into two groups of substances:
** odor carriers – represent the liquid part of the oil-eleoptene;
** odor fixatives – hard at room temperature and odorless, but fix the odor and give it durability-stearoptene. Of the many components of eleoptene with a rosy odor are citronellol, geraniol, nerol, phenylethyl alcohol, but the typical rose odor is also formed by the presence of some characteristic molecules in trace amounts.
** contains: [[ethanol]] (up to 3%), [[linalool]] (1 to 3%), [[phenethyl alcohol]](up to 3%), [[citronellol]] (24 to 35%), [[nerol]] (5 to 12%), [[geraniol]] (13 to 22%), [[geranyl acetate]] (up to 1.5%), [[eugenol]] (up to 2.5%), [[methyl eugenol]] (up to 2%) and [[farnesol]] (at least 1.4%); hydrocarbons – C17 heptadecane (from 1 to 2.5%), C19 saturated hydrocarbon nonadecane CH3 (CH2) 17CH3 (from 8 to 15%), C19 unsaturated hydrocarbon with one or more double carbon bonds nonadecene CH3 (CH2) 16CH = CH2 from 2 to 5%), C21 [[heneicosane]] (from 3 to 5.5%) and C23 [[Higher alkane|tricosane]] (from 0.5 to 1.5%).
*It has a light yellow color with a greenish tinge;
*It resembles almond oil in consistency;
*It has a strong aroma and sharp balsamic taste;
*It has an excellent combination of liquid and solid components.

==References==
{{reflist|2}}

==External links==
*{{wiktionary inline|rose oil}}

{{Rose}}

[[Category:Essential oils]]
[[Category:Roses]]
[[Category:Flavors]]