Cedrol supplier | CasNO.77-53-2

Name
Cedrol
EINECS 201-035-6
CAS No. 77-53-2
Article Data12
CAS DataBase
Density 1 g/cm³
Solubility
Melting Point 55-59 °C(lit.)
Formula C₁₅H₂₆O
Boiling Point 277.2 °C at 760 mmHg
Molecular Weight 222.371
Flash Point 115.5 °C
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-3a,7-Methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-, [3R-(3a,3ab,6a,7b,8aa)]-;8bH-Cedran-8-ol (8CI);Cedrol(6CI,7CI);(+)-Cedrol;a-Cedrol;1H-3a,7-Methanoazulen-6-ol,octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-;
PSA 20.23000
LogP 3.60980

Synthetic route

: 917-54-4
methyllithium

: 52153-97-6
15-nor-3-oxo cedrane

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
In diethyl ether Heating;

: (3R,3aS,6R,7R,8aR)-6-Hydroxy-3,6,8-trimethyl-octahydro-3a,7-methano-azulene-8-carbaldehyde

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
(i) KOH, N2H4, HOCH2CH2OH, (ii) (heating); Multistep reaction;

: (3R,3aS,6R,7R,8aR)-8-Hydroxymethyl-3,6,8-trimethyl-octahydro-3a,7-methano-azulen-6-ol

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3, Py 2: (i) KOH, N2H4, HOCH2CH2OH, (ii) (heating) View Scheme

: 109507-91-7
3-Nor-cedrol

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3, Py 2: diethyl ether / Heating View Scheme

: 40768-85-2, 109312-44-9
3-Norcedr-2-en-3-on

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: diethyl ether / Heating View Scheme

: 76679-86-2, 101262-59-3
(3aR)-2c-acetyl-1,1,4c-trimethyl-(6ac)-hexahydro-pentalene-3ar-carboxylic acid methyl ester

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) LiAlH4, (ii) CrO3, Py, (iii) aq. KOH 2: H2 / Pd-C / ethanol 3: diethyl ether / Heating View Scheme

: 70639-04-2
(3aR)-1.1.4c-trimethyl-(6acH)-hexahydro-3H-pentalene-dicarboxylic acid-(2c.3ar)

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 2: KOH, EtOH / Heating 4: (i) LiAlH4, (ii) CrO3, Py, (iii) aq. KOH 5: H2 / Pd-C / ethanol 6: diethyl ether / Heating View Scheme

: 70639-05-3
(-)-Norcedren-dicarbonsaeuredimethylester

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: KOH, EtOH / Heating 3: (i) LiAlH4, (ii) CrO3, Py, (iii) aq. KOH 4: H2 / Pd-C / ethanol 5: diethyl ether / Heating View Scheme

: (3aR)-1,1,4c-trimethyl-(6acH)-hexahydro-3H-pentalene-dicarboxylic acid-(2c.3ar)-3a-methyl ester

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 2: (i) LiAlH4, (ii) CrO3, Py, (iii) aq. KOH 3: H2 / Pd-C / ethanol 4: diethyl ether / Heating View Scheme

: C19H30O4S2

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: (i) Raney-Ni, (ii) aq. KOH, EtOH, (iii) (racemate resolution using quinine) 3: KOH, EtOH / Heating 5: (i) LiAlH4, (ii) CrO3, Py, (iii) aq. KOH 6: H2 / Pd-C / ethanol 7: diethyl ether / Heating View Scheme

: 372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5
farnesyl pyrophosphate

A: 546-28-1
β-(+)-cedrene

B: 77-53-2
(+)-cedrol

C: 469-61-4
alpha-cedrene

D: 19903-73-2
(-)-(3R,3aS,6S,7R,8aS)-isocedrol

Conditions

Conditions	Yield
With epicedrol synthase In aq. buffer at 30℃; for 1h; pH=8.5; Enzymatic reaction;

...Expand

: 372-97-4, 13058-04-3, 25744-33-6, 27248-37-9, 27248-38-0, 40716-68-5
farnesyl pyrophosphate

: 77-53-2
(+)-cedrol

Conditions

Conditions	Yield
With cedrol synthase gene from the transcriptome of the glandular trichomes of a woody Lamiaceae plant Leucosceptrum canum In aq. buffer at 30℃; for 3h; pH=7.4; Enzymatic reaction;

: 77-53-2
(+)-cedrol

: 16000-39-8
1-cyano-2-methoxynaphthalene

: 2-(((3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl)oxy)-1-naphthonitrile

Conditions

Conditions	Yield
With potassium hexamethylsilazane In 1,4-dioxane at 20℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;	98%

: 74-87-3
methylene chloride

: 77-53-2
(+)-cedrol

: 67874-81-1
cedrol methyl ether

Conditions

Conditions	Yield
Stage #1: (+)-cedrol With potassium tert-butylate In toluene; tert-butyl alcohol at 85 - 110℃; Green chemistry; Stage #2: methylene chloride In tert-butyl methyl ether at 60℃; under 1875.19 Torr; Reagent/catalyst; Temperature; Pressure; Autoclave; Green chemistry;	96.3%

: 912289-98-6
difluorosulfoacetic acid sodium salt

: 77-53-2
(+)-cedrol

: C17H25F2O5S(1-)*Na(1+)

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In toluene for 42h; Reflux;	91%

: 77-53-2
(+)-cedrol

: 105-36-2
ethyl bromoacetate

: C19H32O3

Conditions

Conditions	Yield
Stage #1: (+)-cedrol With sodium hydroxide In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: ethyl bromoacetate In tetrahydrofuran at 25℃; for 6.33333h;	88%

: 77-53-2
(+)-cedrol

: 407-25-0
trifluoroacetic anhydride

: (3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl 2,2,2-trifluoroacetate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	83%

: 77-53-2
(+)-cedrol

: 18319-31-8
(1R,3aS,3bR,6R)-1,3a,6-trimethyl-octahydro-1H-1,6a-cedarane[1,2-c]furan

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; iodine In cyclohexane at 23℃; for 1.5h; Irradiation; Inert atmosphere;	73%
With diphenylselenium hydroxyacetate; iodine In cyclohexane at 50℃; for 12h; Irradiation;	67%
With [bis(acetoxy)iodo]benzene; iodine In cyclohexane at 20℃; for 1.5h; Irradiation; Inert atmosphere; regioselective reaction;

: 77-53-2
(+)-cedrol

: 67152-03-8
(3S,3aR,6R,7R,8aS) -3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene-3,6-diol

Conditions

Conditions	Yield
Stage #1: (+)-cedrol With cis-RuCl2(4,4'-di-tert-butyl-2,2'-bipyridine)2; acetic acid In water for 0.0333333h; Darkness; Stage #2: With periodic acid In water for 4h; Darkness; chemoselective reaction;	55%
With iodosylbenzene; C40H39ClN4OPRu(1+)*Cl(1-); trifluoroacetic acid In 1,1,2,2-tetrachloroethane at 35℃; for 18h; regioselective reaction;	53%
With 1,3,5-trichlorobenzene; iodosylbenzene; C38H35ClN4OPRu(1+)*Cl(1-); trifluoroacetic acid In 1,1,2,2-tetrachloroethane at 30℃; for 48h;	36.5%
With ammonium cerium (IV) nitrate; 2C7H7O3S(1-)*C20H30N4O2Ru(2+) In water; tert-butyl alcohol at 20℃; for 0.666667h;

: 63527-43-5
2,3,5-p-Nitrobenzoyl-D-ribofuranosylbromid

: 77-53-2
(+)-cedrol

: 99049-93-1
(Cedran-8-yl)-2,3,5-tri-O-(p-nitrobenzoyl)-β-D-ribofuranosid

Conditions

Conditions	Yield
With molecular sieve; silver silicate In dichloromethane for 24h;	43%

: 77-53-2
(+)-cedrol

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 99049-91-9
(Cedran-8-yl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosid

Conditions

Conditions	Yield
With calcium sulfate; silver carbonate In dichloromethane for 1.5h; Ambient temperature;	40%

: 39998-25-9
methyl pyridine-3-acetate

: 77-53-2
(+)-cedrol

: (1S,2R,5S,8R)-cedryl 3-pyridylacetate

Conditions

Conditions	Yield
With n-butyllithium In hexane for 24h; Ambient temperature;	38%

: 77-53-2
(+)-cedrol

A: 142864-21-9
((3aR)-1.1.4c-trimethyl-2c-acetyl-(6acH)-hexahydro-3H-pentalenyl-(3ar))-acetic acid

B: 67152-03-8
(3S,3aR,6R,7R,8aS) -3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene-3,6-diol

Conditions

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 70℃; for 24h;	A n/a B 29%

: 77-53-2
(+)-cedrol

: 75-24-1
trimethylaluminum

: C34H62Al2O2

Conditions

Conditions	Yield
With 4-Fluorobenzoic acid In octane at 85℃; for 144h;	28%

: 77-53-2
(+)-cedrol

: 140-88-5
ethyl acrylate

: ethyl 3-((3R,3aS,6S,7S,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl)propanoate

Conditions

Conditions	Yield
With cyclopentadienyl titanium(IV) trichloride; triethylsilyl chloride; zinc In tetrahydrofuran at 60℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere; enantioselective reaction;	27%

: 77-53-2
(+)-cedrol

: 22860-91-9
2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide

: 99049-94-2
(Cedran-8-yl)-2,3,5-tri-O-benzoyl-β-D-ribofuranosid

Conditions

Conditions	Yield
With molecular sieve; silver silicate In dichloromethane for 1h;	14%

: 29800-89-3
methyl 4-pyridineacetate

: 77-53-2
(+)-cedrol

: (1S,2S,5S,8R)-cedryl 4-pyridylacetate

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane for 24h; Ambient temperature;	13%

: 77-53-2
(+)-cedrol

A: 50539-24-7
3α,8β-dihydroxycedrane

B: 67152-03-8
(3S,3aR,6R,7R,8aS) -3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene-3,6-diol

C: 3β,8β-dihydroxycedrane

D: 8β,12-dihydroxycedrane

Conditions

Conditions	Yield
With Mucor plumbeus In ethanol for 144h; Further byproducts given;	A 5 mg B 3% C 5 mg D 2%

...Expand

: 77-53-2
(+)-cedrol

A: 50539-24-7
3α,8β-dihydroxycedrane

B: 67152-03-8
(3S,3aR,6R,7R,8aS) -3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene-3,6-diol

C: 3β,8β-dihydroxycedrane

D: 8β,12-dihydroxycedrane

E: 3β,8β,10-trihydroxycedrane

Conditions

Conditions	Yield
With Mucor plumbeus In ethanol for 144h; Product distribution; microbiological hydroxylation of cedrol and related compounds by Mucor plumbeus;	A 5 mg B 3% C 6 mg D 2% E n/a

...Expand

: 77-53-2
(+)-cedrol

: 8-β-hydroxycedran-10-one

Conditions

Conditions	Yield
With pyridine; zinc; Fe3O(OAc)6Pyr3.5 In water; acetic acid for 6h; Ambient temperature;	1.3%

: 64-18-6
formic acid

: 77-53-2
(+)-cedrol

: 469-61-4
(-)-α-cedrene

: 77-53-2
(+)-cedrol

: 53684-57-4
N-chlorobetainyl chloride

: O-trimethylammonioacetyl-cedrol; chloride

Conditions

Conditions	Yield
With chloroform; N,N-dimethyl-aniline

: 77-53-2
(+)-cedrol

: (8aS)-6c-(3.5-dinitro-benzoyloxy)-3c.6t.8.8-tetramethyl-(8arH)-octahydro-3H-3at.7t-methano-azulene

Cedrol Chemical Properties

The Molecular Structure of Cedrol (CAS NO.77-53-2):

Molecular Formula C₁₅H₂₆O
Molecular Weight 222.37
Melting Point: 55-59°C
Boiling Point: 273°C
Flash Point: 200 ºF
Product Categories: Industrial/Fine Chemicals
Synonyms: (+)-Cedrol ; AI3-02178 ; Cedarwood oil alcohols ; Cedrol (natural) ; EINECS 201-035-6 ; EUDESMOL ; UNII-63ZM9703BO ; a-Cedrol ; (3R-(3alpha,3Abeta,6alpha,7beta,8aalpha))-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol ; 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl- ; (3R,3aS,6R,7R,8aS)- 8-betaH-Cedran-8-ol (8CI) 8betaH-Cedran-8-ol (8CI) Cedrol (6CI,7CI)

Cedrol Uses

Cedrol (CAS NO.77-53-2) can be used as a perfume fixative for variety of cosmetic compunds and the materials of Cedryl Acetate and Methyl Cedryl Ether etc.

Cedrol Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intraperitoneal	> 500mg/kg (500mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 8, Pg. 102, 1956.
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 745, 1975.

Cedrol Safety Profile

Safety Statements: 22-24/25
S22: Do not breathe dust
S24/25: Avoid contact with skin and eyes
WGK Germany: 2
RTECS: PB7728666
Human experience: 8 % solution: no irritation or sensitization.
Maximised Survey-derived Daily Intakes (MSDI-EU) : 13.00 (μg/capita/day)
modified Theoretical Added Maximum Daily Intake (mTAMDI) : 3900 (μg/person/day)
Threshold of concern : 1800 (μg/person/day)
R 36/37/38: Irritating to eyes, respiratory system, and skin.
S 02: Keep out of the reach of children.
S 24/25: Avoid contact with skin and eyes.
S 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36: Wear suitable protective clothing.
Dermal Toxicity(LD50): Skin-Rabbit >5.00 gm/kg

Product Name

Cedrol

Synthetic route

Cedrol Chemical Properties

Cedrol Uses

Cedrol Toxicity Data With Reference

Cedrol Safety Profile

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