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Cas Database

Name	Ambroxane	EINECS	229-861-2
CAS No.	6790-58-5	Density	0.939 g/cm³
PSA	9.23000	LogP	4.40800
Solubility	1.88mg/L at 20℃	Melting Point	73-77 °C
Formula	C₁₆H₂₈O	Boiling Point	273.9 °C at 760 mmHg
Molecular Weight	236.398	Flash Point	104.8 °C
Transport Information	N/A	Appearance	white crystals
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	Naphtho[2,1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-, [3aR-(3aa,5ab,9aa,9bb)]-;(-)-Ambrox;(-)-Ambroxan;(-)-Ambroxide;(-)-Norlabdane oxide;Amberlyn Super;Amberlyn Super PM 577;Ambroxide;	Article Data	66

Ambroxane Synthetic route

: 564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5
(3aR)-(+)-sclareolide

A: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

B: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With RuCl2(2-(diphenylphosphino)-N-(thiophen-2-ylmethyl)ethanamine)PPh3; hydrogen In toluene at 100℃; under 37503.8 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Autoclave;	A 99.5% B n/a
With RuCl2(2-(diphenylphosphino)-N-(2-(methylthio)ethyl)ethanamine)PPh3; hydrogen; sodium methylate In toluene at 100℃; for 16h; Catalytic behavior; Autoclave;	A 67% B 12%

: 320756-17-0
biscyclohomofarnesane-8α,12-diol

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 11h;	98%

: 10207-83-7, 38419-75-9, 41747-05-1, 55881-96-4, 64090-93-3, 86023-44-1, 86023-45-2, 100679-84-3, 105087-83-0, 106035-74-9, 106091-98-9, 106091-99-0, 122566-14-7, 131831-64-6, 131831-66-8, 131831-67-9, 131831-74-8
(8α-Methyl)-iresan-8β,11-diol

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 10h;	97%

: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With n-butyllithium; p-toluenesulfonyl chloride In tetrahydrofuran; hexane at 0 - 20℃;	96%
With sodium hydride; p-toluenesulfonyl chloride In dichloromethane at 25℃;	94%
With zinc(II) chloride In 1,2-dichloro-ethane for 3h;	92%

: 1038482-07-3
Δ2(3)-ambrox

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen In ethyl acetate at 20℃; for 12h;	96%
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr;	92%

aqueous sodium sulfate: aqueous sodium sulfate

: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With hydrogenchloride In water; toluene	95%

: 121067-50-3
<1R-(1α,2β,4aβ,8aα)>-decahydro-1-(2-chloroethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol	92%

: 116163-57-6
(3aS,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-4-one

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine	90%

: 564-20-5, 1216-84-8, 30450-17-0, 58976-28-6, 64090-92-2, 67844-42-2, 79768-41-5, 79768-42-6, 86688-27-9, 86688-28-0, 95406-08-9, 98719-44-9, 98719-46-1, 131831-65-7, 140851-80-5
(3aR)-(+)-sclareolide

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With sodium tetrahydroborate; zinc(II) iodide In tetrahydrofuran for 1h; Heating;	85%
Multi-step reaction with 2 steps 1: 95 percent / potassium borohydride / ethanol / 10 h / Heating 2: 92 percent / bromotrichloromethane; triphenylphosphine; NaHCO3 / CH2Cl2 / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 2: 96 percent / n-BuLi; TsCl / hexane; tetrahydrofuran / 0 - 20 °C View Scheme

: 121067-46-7
<1R-(1α,2β,4aβ,8aα)>-1-decahydro-1-(2-iodoethyl)-2,5,5,8a-tetramethyl-2-naphthalenol acetate

: 6790-58-5
(-)-ambroxide

Conditions

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol for 18h; Heating;	81%

Ambroxane Chemical Properties

Molecular Structure of Ambroxide (CAS NO. 6790-58-5):

EINECS: 229-861-2
Systematic Name: 3a,6,6,9a-Tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e]benzofuran
Molecular Formula: C₁₆H₂₈O
Molecular Weight: 236.3929
SMILES: O2C1(CCC3C(C1CC2)(C)CCCC3(C)C)C
InChI: InChI=1/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3
InChIKey: YPZUZOLGGMJZJO-UHFFFAOYAI
Index of Refraction: 1.48
Molar Refractivity: 71.59 cm³
Molar Volume: 251.6 cm³
Surface Tension: 34.6 dyne/cm
Density: 0.939 g/cm³
Flash Point: 104.8 °C
Enthalpy of Vaporization: 49.16 kJ/mol
Boiling Point: 273.9 °C at 760 mmHg
Vapour Pressure: 0.00934 mmHg at 25 °C
Melting Point: 74-76 °C(lit.)
Water Solubility: 2.436 mg/L at 25 °C
Alpha: -30 º (c=1% in toluene )

Ambroxane Safety Profile

Safety Information of Ambroxide (CAS NO. 6790-58-5):
WGK Germany: 1

Ambroxane Specification

Ambroxide with cas registry number of 6790-58-5 is colorless to white crystalline solid, known as 8alpha,12-Oxido-13,14,15,16-tetranorlabdane ; Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, (3aR-(3aalpha,5abeta,9aalpha,9bbeta))- ; FEMA No. 3471 ; Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR-(3aalpha,5abeta,9aalpha,9bbeta))- ; (3AR-(3aalpha,5abeta,9aalpha,9bbeta))-dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan ; Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)- ; 1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(sup 4,9))tridecane . It is used in flavor of advanced perfumes and cosmetics.

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