Β-Santalol

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β-Santalol
Beta-santalol PubChem6857681.svg
Names
Preferred IUPAC name
(2Z)-2-Methyl-5-[(1S,2R,4R)-2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-yl]pent-2-en-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.935 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-027-2
KEGG
PubChem CID
UNII
  • InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)12(2)13-6-7-14(15)9-13/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5-/t13-,14+,15+/m1/s1
    Key: OJYKYCDSGQGTRJ-GQYWAMEOSA-N
  • C/C(CO)=C\CCC2(C)C(=C)C1CC2CC1
Properties
C15H24O
Molar mass 220.356 g·mol−1
AppearanceLiquid
Density 0.9717 g/cm3
Boiling point 177 °C (351 °F; 450 K)
Practically insoluble
Solubility in ethanol Soluble
Solubility in diethyl ether Soluble
−87.1°
1.5100
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
Related compounds
Related terpenes
α-Santalol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

β-Santalol is an organic compound that is classified as a sesquiterpene. It comprises about 20% of the oil of sandalwood, the major component being α-santalol. In 2002, about 60 tons of sandalwood oil were produced by steam distillation of the heartwood of Santalum album . [1]

Because of concerns about the sustainability of sandalwood tree cultivation, scientists have developed routes to α-santalol and β-santalol via fermentation, including using Rhodobacter sphaeroides . BASF launched its version, Isiobionic Santalol, in July 2020. [2]

Related Research Articles

Alpha–beta pruning is a search algorithm that seeks to decrease the number of nodes that are evaluated by the minimax algorithm in its search tree. It is an adversarial search algorithm used commonly for machine playing of two-player combinatorial games. It stops evaluating a move when at least one possibility has been found that proves the move to be worse than a previously examined move. Such moves need not be evaluated further. When applied to a standard minimax tree, it returns the same move as minimax would, but prunes away branches that cannot possibly influence the final decision.

<span class="mw-page-title-main">Sandalwood</span> Class of woods from trees in the genus Santalum

Sandalwood is a class of woods from trees in the genus Santalum. The woods are heavy, yellow, and fine-grained, and, unlike many other aromatic woods, they retain their fragrance for decades. Sandalwood oil is extracted from the woods. Sandalwood is often cited as one of the most expensive woods in the world. Both the wood and the oil produce a distinctive fragrance that has been highly valued for centuries. Consequently, some species of these slow-growing trees have suffered over-harvesting in the past.

Negamax search is a variant form of minimax search that relies on the zero-sum property of a two-player game.

<span class="mw-page-title-main">Pinene</span> Oily organic chemical found in plants

Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major component of the liquid extracts of conifers. Pinenes are also found in many non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush.

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

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

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

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.

<span class="mw-page-title-main">Copaiba</span> Resin and essential oil from South American Copaifera trees

Copaiba is a stimulant oleoresin obtained from the trunk of several pinnate-leaved South American leguminous trees. The thick, transparent exudate varies in color from light gold to dark brown, depending on the ratio of resin to essential oil. Copaiba is used in making varnishes and lacquers.

<i>Santalum spicatum</i> Australian sandalwood

Santalum spicatum, the Australian sandalwood, also Waang and other names (Noongar) and Dutjahn (Martu), is a tree native to semi-arid areas at the edge of Southwest Australia, in the state of Western Australia. It is also found in South Australia, where it is protected and listed as a vulnerable species. It is traded as sandalwood, and its sandalwood oil has been used as an aromatic and a food source over history. S. spicatum is one of four Santalum species occurring in Australia.

β-Pinene Chemical compound

β-Pinene is a monoterpene, an organic compound found in plants. It is one of the two isomers of pinene, the other being α-pinene. It is colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

<span class="mw-page-title-main">Cannabis flower essential oil</span> Essential oil obtained from the hemp plant

Cannabis flower essential oil, also known as hemp essential oil, is an essential oil obtained by steam distillation from the flowers, panicles, stem, and upper leaves of the hemp plant. Hemp essential oil is distinct from hemp seed oil and hash oil: the former is a vegetable oil that is cold-pressed from the seeds of low-THC varieties of hemp, the latter is a THC-rich extract of dried female hemp flowers (marijuana) or resin (hashish).

The molecular formula C15H24O may refer to:

<i>Santalum album</i> Species of tree in Sandalwood family

Santalum album, or Indian sandalwood, is a small tropical tree, and the traditional source of sandalwood oil. It is native to southern India and Southeast Asia. It is considered sacred in some religions like Hinduism, and some cultures place great significance on its fragrant qualities. However, the high value of the species has caused over-exploitation, to the point where the wild population is vulnerable to extinction. Indian sandalwood still commands high prices for its essential oil owing to its high alpha santalol content, but due to lack of sizable trees it is no longer used for fine woodworking as before. The plant is long-lived, but harvest is only viable after many years.

<i>Cryptocarya agathophylla</i>

Cryptocarya agathophylla is a member of the laurel family, Lauraceae, and originates in Madagascar.

Santanol may refer to either of two isomers of the sesquiterpene alcohol making up sandalwood oil, from Santalum species:

α-Santalol Chemical compound

α-Santalol, also referred to as alpha-santalol, is an organic compound that is classified as a sesquiterpene. It comprises about 55% of the oil of sandalwood, another less abundant component being β-santalol. As of 2002, about 60 tons of sandalwood oil are produced annually by steam distillation of the heartwood of Santalum album. It is a valued component for perfumes.

<span class="mw-page-title-main">Tree allometry</span> Quantitative relations between some key characteristic dimensions of trees

Tree allometry establishes quantitative relations between some key characteristic dimensions of trees and other properties. To the extent these statistical relations, established on the basis of detailed measurements on a small sample of typical trees, hold for other individuals, they permit extrapolations and estimations of a host of dendrometric quantities on the basis of a single measurements.

<span class="mw-page-title-main">Sandalwood oil</span> Essential oil

Sandalwood oil is an essential oil obtained from the steam distillation of chips and billets cut from the heartwood of various species of sandalwood trees, mainly Santalum album and Santalum spicatum.

<i>Croton sylvaticus</i> Species of flowering plant

Croton sylvaticus is a tree in the family Euphorbiaceae. It is commonly known as the forest fever-berry. These trees are distributed in forests from the east coast of South Africa to Tropical Africa. It grows 7–13 metres (23–43 ft) in height, occasionally up to 30 metres (100 ft), in moist forests, thickets and forest edges at altitudes of 350–1,800 metres (1,100–5,900 ft).

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

Isobornyl cyclohexanol is an organic compound used primarily as a fragrance because of its aroma which is similar to sandalwood oil. Its chemical structure is closely related to that of both α-Santalol and β-Santalol, which are the primary constituents of sandalwood oil.

<span class="mw-page-title-main">Mysore Sandalwood Oil</span>

Mysore Sandalwood Oil is a trademarked perfume oil extracted from the Santalum album variety of sandalwood tree in the Mysore district of Karnataka, India. The tree species is said to be one of the best varieties in the world.

References

  1. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; doi : 10.1002/14356007.a11_141.
  2. Bettenhausen, Craig (November 11, 2021). "Making sandalwood oil without sandalwood trees". Chemical & Engineering News. Retrieved Feb 11, 2021.