CEDROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H26O
Molecular Weight	222.3663
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@H](C)[C@]13C[C@H](C2(C)C)[C@](C)(O)CC3

InChI

InChIKey=SVURIXNDRWRAFU-OGMFBOKVSA-N

InChI=1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H26O
Molecular Weight	222.3663
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18640184

Cedrol is a sesquiterpene alcohol found in the essential oil of conifers (cedar oil), especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano. Cedrol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its use worldwide is in the region of 1–10 metric tonnes per annum. The maximum skin level in formulae that go into fine fragrances has been reported to be 1.51% assuming use of the fragrance oil at levels up to 20% in the final product. The 97.5 percentile use level in formulae for use in cosmetics in general has been reported to be 1.3%, which would result in a maximum daily exposure on the skin of 0.0331 mg/kg for high end users of these products. Finding the natural source of this compound might help to elucidate why Anopheles gambiae and Anopheles arabiensis prefer to lay eggs in habitats containing it. Cedrol is the first compound confirmed as an oviposition attractant for gravid An. gambiae s.l. This finding paves the way for developing new ‘attract and kill strategies’ for malaria vector control.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15742349	Antagonist 2778		10.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Antitermitic activity of essential oils and components from Taiwania (Taiwania cryptomerioides).	2001 Apr	11446295
[Studies on the chemical components from Sargassum fusiform].	2001 Jul	11668740
Inhibition of platelet-activating factor receptor binding by aporphine and phenanthrenoid alkaloids from Aromadendron elegans.	2001 Jul	11488464
Biotransformation of cedrol by Curvularia lunata ATCC 12017.	2001 Mar	11261573
Antimicrobial activity of some Pacific Northwest woods against anaerobic bacteria and yeast.	2001 Nov	11746838
The sedative effects and mechanism of action of cedrol inhalation with behavioral pharmacological evaluation.	2003 Jul	12898420
Volatile constituents of the fruit and leaf oils of Thuja orientalis L. grown in Iran.	2003 Mar-Apr	12710722
Crystal structure of 1beta-hydroxy-beta-homopipitzolone (9-hydroxy-2,6,9-trimethyltricyclo[6,3,1,0(1,6)]dodeca-5,10,11,12-tetraone).	2003 May	12769389
Stereospecific hydroxylation of (+)-cedrol by using human skin microbial flora Staphylococcus epidermidis.	2003 Oct	14526908
Autonomic responses during inhalation of natural fragrance of Cedrol in humans.	2003 Oct 31	14614968
Pressurized fluids for extraction of cedarwood oil from Juniperus virginianna.	2004 Apr 21	15080642
Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.	2004 Dec	15637231
New terpenoids in cultivated and wild chamomile (in vivo and in vitro).	2004 Feb 5	14698259
Intramolecular iron-mediated diene/olefin cyclocoupling: formation of carbon spirocycles.	2004 Jul 22	15255684
[Terpenoids in root exudates of different allelopathic rice varieties].	2005 Apr	16011177
[Chemical components and antimicrobial activity of essential oils in Cunninghamia lanceolata heartwood].	2005 Dec	16515195
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.	2005 May	17192005
[Studies on the chemical constituents in root of Coleus forskohlii].	2005 Nov	16468372
Reduction of infectivity of schistosome cercariae by application of cercaricidal oil to water.	2005 Nov	16282311
Assessment of pulse rate variability by the method of pulse frequency demodulation.	2005 Nov 1	16259639
Chemical composition, cytotoxic activity and antimicrobial activity of essential oils of leaves and berries of Juniperus phoenicea L. grown in Egypt.	2007 Jun 10	20161910
Overseas survey of the effect of cedrol on the autonomic nervous system in three countries.	2007 May	17641454
Eudismic analysis of tricyclic sesquiterpenoid alcohols: lead structures for the design of potent inhibitors of the human UDP-glucuronosyltransferase 2B7.	2007 Oct	17706742
A new labdane-type diterpene from the bark of Juniperus chinensis Linn.	2008	18855216
A gold-catalyzed entry into the sesquisabinene and sesquithujene families of terpenoids and formal total syntheses of cedrene and cedrol.	2008	18785666
Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.	2008 Dec	19067375
Antiproliferative effects of essential oils and their major constituents in human renal adenocarcinoma and amelanotic melanoma cells.	2008 Dec	19040575
Effects of direct cedrol inhalation into the lower airway on autonomic nervous activity in totally laryngectomized subjects.	2008 Feb	17953722
Woody pretzels: spirocycles from vetiver to patchouli and Georgywood.	2008 Jun	18618805
Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya.	2008 Mar-Apr	18533464
Fragrance material review on cedrol.	2008 Nov	18640184
[Electroantennogram responses of Maruca testulalis (Lepidoptera: Pyralidae) to plant volatiles and sex pheromone].	2009 Aug	19947220
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.	2009 Feb	19212980
Biotransformation of alpha-cedrol and caryophyllene oxide by the fungus Neurospora crassa.	2010 Apr	20433062
Antiplatelet aggregation and platelet activating factor (PAF) receptor antagonistic activities of the essential oils of five Goniothalamus species.	2010 Jul 29	20714290
Relation between developmental stage, sensory properties, and volatile content of organically and conventionally grown pac choi (Brassica rapa var. Mei Qing Choi).	2010 May	20546419
Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation.	2010 Nov 3	21060292

Patents

Sample Use Guides

In Vivo Use Guide

The maximum skin level in formulae that go into fine fragrances has been reported to be 1.51% assuming use of the fragrance oil at levels up to 20% in the final product. The 97.5 percentile use level in formulae for use in cosmetics in general has been reported to be 1.3%, which would result in a maximum daily exposure on the skin of 0.0331 mg/kg for high end users of these products

Route of Administration: Topical

In Vitro Use Guide

Anopheles gambiae species females were two times more likely to lay eggs in lake water infused for six days with soil from a natural oviposition site in western Kenya compared to lake water alone or to the same but autoclaved infusion. One of the soil infusion volatiles was readily identified as the sesquiterpene alcohol cedrol. Its widespread presence in natural aquatic habitats in the study area was confirmed by analysing the chemical headspace of 116 water samples collected from different aquatic sites in the field and was therefore selected for evaluation in oviposition bioassays. Twice as many gravid females were attracted to cedrol-treated water than to water alone in two choice cage bioassays and in experiments conducted in large-screened cages with free-flying mosquitoes. When tested in the field, wild malaria vector females were three times more likely to be collected in the traps baited with cedrol than in the traps containing water alone.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:34:45 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:45 GMT 2023`
Record UNII	63ZM9703BO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEDROL

Official Name

English

(3R-(3.ALPHA.,3A.BETA.,6.ALPHA.,7.BETA.,8A.ALPHA.))-OCTAHYDRO-3,6,8,8-TETRAMETHYL-1H-3A,7-METHANOAZULEN-6-OL

Common Name

English

(+)-CEDROL

Common Name

English

CEDROL [INCI]

Common Name

English

CEDAR CAMPHOR

Common Name

English

CEDROL [MI]

Common Name

English

NSC-403883

Code

English

CYPRESS CAMPHOR

Common Name

English

8.BETA.H-CEDRAN-8-OL

Common Name

English

FEMA NO. 4503

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

(+)-CEDROL