Cedrol

Structural formula
General
Surname	Cedrol
other names	(+) - Cedrol; 3-cedranol; β-cedrol; (1 S , 2 R , 5 S , 7 R , 8 R ) -2,6,6,8-tetramethyltricyclo [5.3.1.0 1.5 ] undecan-8-ol; Octahydro-3,6,8,8-tetramethyl-1 H -3a, 7-methanoazulen-6-ol; CEDROL ( INCI ) ;
Molecular formula	C 15 H 26 O
External identifiers / databases
EC number	201-035-6
ECHA InfoCard	100,000,942
PubChem	65575
ChemSpider	59018
Wikidata	Q1052617
properties
Molar mass	222.37 g mol −1
Physical state	firmly
Melting point	86-87 ° C
boiling point	273 ° C
solubility	soluble in chloroform
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The cedrol is a terpenoid natural products .

Occurrence

Common Juniper ( Juniperus communis )

Cedrol is widespread and is found in the essential oil of pine-like plants ( Pinales ), especially in cypresses ( Cupressus ) and juniper ( Juniperus ). It has also been identified as an ingredient in Dost (e.g. Origanum smyrnaeum , also known as Origanum onites ).

Properties and structure

Cedrol is a sesquiterpene that is biosynthetically derived from ferns and is a common member of a group of terpenes , the cedran.

Basic structure	Application to the Cedrol	Explanation
		Biosynthetically derived numbering
		Azulene-derived numbering ( CAS )
		Numbering derived from undecane ( IUPAC )

Cedrol is a good way to show differences in the nomenclature of cedranas and natural products in general. In the present example there are three nomenclature systems. First the naming according to phytochemical principles : the name according to the original source (in this case the cedar) and the numbering according to the biochemical predecessor Farnese . In the second and third example, strict chemical procedures are demonstrated. It is the simplification of the molecule into a basic structure. This basic structure is the azulene for the purposes of the Chemical Abstracts Service , while the IUPAC regards the backbone of the cedrane as a carbon cycle with eleven atoms and describes it as undecane . What must be treated with great caution in this context is the numbering of the substituents, especially when comparing related or the same structures between the different nomenclatures. In the case of the Cedrane, it can be very interesting because even the IUPAC sometimes uses the trivial name "Cedrane" - but with the counting method derived from the Undecane model. In this context it should be noted that “Eudesmol” is sometimes mistakenly used as a synonym for “Cedrol”.

Eudesmol

The chemical synthesis of cedrol is summarized several times in the literature and its main application is in aroma chemistry.

Biological importance

Cedrol is attracting interest because of its toxicity and possible carcinogenic properties.

Individual evidence

↑ Entry on CEDROL in the CosIng database of the EU Commission, accessed on June 9, 2020.
↑ ^a ^b The Merck Index. 12th edition. Merck Research Laboratories, 1996, ISBN 0-911910-12-3 , entry 1961.
↑ DR Lide (Ed.): Handbook of Chemistry and Physics. 78th edition. CRC Press, 1997-1998, ISBN 0-8493-0478-4 , entry 7570, pp. 3-208.
↑ ^a ^b data sheet (+) - Cedrol at Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).
↑ JD Connolly, RA Hill (Ed.): Dictionary of Terpenoids Volume 1 Mono- and sesquiterpenoids. Chapman & Hall, 1991, ISBN 0-412-25770-X , entry SQ02555.
↑ Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)
^ EJ Corey, XM Cheng: The Logic of Chemical Synthesis. Wiley, 1989, ISBN 0-471-50979-5 , pp. 4-5, 156-158.
↑ E. Breitmeier: Terpenes: flavors, fragrances, pharmaca, pheromones. Wiley-VCH, 2006, ISBN 3-527-31786-4 , pp. 46-47.
↑ JR Sabine: Exposure to an environment containing the aromatic red cedar, Juniperus virginiana: procarcinogenic, enzyme-inducing and insecticidal effects . In: Toxicology . tape 5 , no. 2 , 1975, p. 221-235 , PMID 174251 .

[CosIng-1] Entry on CEDROL in the CosIng database of the EU Commission, accessed on June 9, 2020.

[Merck_12_1961-2] The Merck Index. 12th edition. Merck Research Laboratories, 1996, ISBN 0-911910-12-3 , entry 1961.

[CRC_78_7570-3] DR Lide (Ed.): Handbook of Chemistry and Physics. 78th edition. CRC Press, 1997-1998, ISBN 0-8493-0478-4 , entry 7570, pp. 3-208.

[SiAl-4] ta sheet (+) - Cedrol at Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).

[DOT_V1_Sq02555-5] JD Connolly, RA Hill (Ed.): Dictionary of Terpenoids Volume 1 Mono- and sesquiterpenoids. Chapman & Hall, 1991, ISBN 0-412-25770-X , entry SQ02555.

[IUPAC_Cedrane-6] Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)

[Corey_Logic-7] EJ Corey, XM Cheng: The Logic of Chemical Synthesis. Wiley, 1989, ISBN 0-471-50979-5 , pp. 4-5, 156-158.

[TFF_46-8] E. Breitmeier: Terpenes: flavors, fragrances, pharmaca, pheromones. Wiley-VCH, 2006, ISBN 3-527-31786-4 , pp. 46-47.

[Sabine_1975-9] JR Sabine: Exposure to an environment containing the aromatic red cedar, Juniperus virginiana: procarcinogenic, enzyme-inducing and insecticidal effects . In: Toxicology . tape 5 , no. 2 , 1975, p. 221-235 , PMID 174251 .