CAS No.4674-50-4,NOOTKATONE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	4674-50-4
Name:	NOOTKATONE
Article Data:	45

Formula:	C₁₅H₂₂O
Molecular Weight:	218.339
Synonyms:	(4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one;(4R,4aS,6R)-4,4a-Dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one;
EINECS:	225-124-4
Density:	0.96 g/cm³
Melting Point:	36-37 °C
Boiling Point:	318.6 °C at 760 mmHg
Flash Point:	142.1 °C
Solubility:	Slightly soluble in ethanol and chloroform. Partly soluble in water.
Appearance:	colourless crystal
Safety:	23-24/25
PSA:	17.07000
LogP:	3.90420

Synthetic route

: 72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With sodium acetate In water; acetic acid at 100℃; for 2h;	93%
With sodium acetate; acetic acid at 100℃; for 2h; Inert atmosphere;	93%
With sodium acetate; acetic acid at 100℃; for 2h;	93%
With aluminum oxide In hexane at 60℃; for 24h; Yield given;

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

: 563-41-7
semicarbazide hydrochloride

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
Stage #1: valencene With manganese(IV) oxide In dichloromethane at -25℃; for 0.5h; Stage #2: With tert.-butylhydroperoxide In dichloromethane; water at -10℃; for 9h; Reflux; Stage #3: semicarbazide hydrochloride Further stages;	83%

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With Czapek-pepton medium; Pallavicinia subcilita at 30℃; for 168h; pH=7.0;	82%
With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate In acetone Reagent/catalyst; Solvent; Electrochemical reaction; chemoselective reaction;	77%
With tert.-butylhydroperoxide; sodium chlorite In water; acetonitrile at 50℃; for 18h; Product distribution / selectivity;	72%

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 136918-14-4
phthalimide

B: 4674-50-4
(+)-nootkatone

C: 840474-83-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions

Conditions	Yield
With oxygen; N-hydroxyphthalimide; cobalt nitrate; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 3h; Product distribution / selectivity;	A n/a B 67.9% C 5.6%
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 4h; Product distribution / selectivity;	A n/a B 53.7% C 1.4%

...Expand

: 329309-57-1
(4R,4aS,6R)-2-hydroperoxy-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalene

A: 4674-50-4
(+)-nootkatone

B: 840474-83-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions

Conditions	Yield
With lyophilisate of Pleurotus sapidus In aq. buffer at 20℃; for 48h; pH=7.4; Enzymatic reaction;	A 16% B 7%

: 17334-55-3
β-gurjunene

A: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

B: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With culture medium of Mucor species; Czapek-pepton medium at 30℃; for 168h;	A 0.7% B 0.6%

: 20489-50-3
(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With pyridine; trichlorophosphate

: 72453-44-2
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

A: 15764-04-2
(4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one

B: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
With aluminum oxide In hexane at 60℃; for 24h;

: 10219-75-7, 22343-24-4, 24741-64-8, 68773-84-2, 4630-07-3
valencene

A: 50763-63-8
(2R,4aR,8R,8aS)-2-Isopropenyl-8,8a-dimethyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ol

B: 50763-66-1
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

C: 50763-67-2
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

D: 4674-50-4
(+)-nootkatone

E: 32420-34-1, 32420-35-2, 50763-64-9, 50763-65-0, 53643-08-6
(4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol

Conditions

Conditions	Yield
Mechanism; Product distribution; multistep reaction: photooxygenation + reduction; reaction with triplet and singlet oxygen;

...Expand

: 67779-29-7
2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

: 3102-33-8
trans-3-penten-2-one

: 4674-50-4
(+)-nootkatone

Conditions

Conditions	Yield
(i) KOtBu, tBuOH, (ii) aq. KOH; Multistep reaction;

Raw Materials

Downstream Products

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Specification

The 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-, with the CAS registry number 4674-50-4, is also known as (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one. It belongs to the product categories of Chiral Building Blocks; Ketones; Organic Building Blocks. Its EINECS registry number is 225-124-4. The molecular formula of this chemical is C₁₅H₂₂O and molecular weight is 218.3346. What's more, its IUPAC name is (4R,4aS,6R)-4,4a-Dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one. In addition, it should be stored in condition of cold, dry and inclosed. And it is stable in condition of normal temperature and pressure. It is colourless crystal. When you are dealing with this chemical, you should be very careful. Avoid contacting with skin and eyes. Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer).

Physical properties about 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-e are: (1)ACD/LogP: 3.84; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.84; (4)ACD/LogD (pH 7.4): 3.84; (5)ACD/BCF (pH 5.5): 487.98; (6)ACD/BCF (pH 7.4): 487.98; (7)ACD/KOC (pH 5.5): 2923.88; (8)ACD/KOC (pH 7.4): 2923.88; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.503; (14)Molar Refractivity: 66.71 cm³; (15)Molar Volume: 225.4 cm³; (16)Polarizability: 26.44×10^-24cm³; (17)Surface Tension: 32.5 dyne/cm; (18)Density: 0.96 g/cm³; (19)Flash Point: 142.1 °C; (20)Enthalpy of Vaporization: 56.01 kJ/mol; (21)Boiling Point: 318.6 °C at 760 mmHg; (22)Vapour Pressure: 0.000358 mmHg at 25 °C; (23) Melting Point: 36-37 °C; (24)Fp: 99 °C; (25)Refractive index: n20/D 1.52.

Preparation of 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-: this chemical can be prepared by (+-)-Valencen. This reaction needs reagent CrO₃*(Pyridine)₂ and solvent CH₂Cl₂. The reaction time is 12 hours. The yield is 80%.

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- can be prepared by (+-)-Valencen.

Use of 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-: it can react with 1,2-Ethanedithiobis(trimethylsilane) to give C₁₇H₂₆S₂.The reaction occurs with reagent ZnI₂ and solvent Diethyl ether. This reaction time is 14 hours. The yield is 93 %.

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- can react with 1,2-Ethanedithiobis(trimethylsilane) to give C17H26S2.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2\C=C1\CC[C@@H](\C(=C)C)C[C@@]1(C)[C@H](C)C2
(2) InChI: InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
(3) InChIKey: WTOYNNBCKUYIKC-JMSVASOKBQ