Ambrox

Product Name:

Ambrox，Ambroxane

Synonyms:

1,5,5,9-TETRAMETHYL-13-OXATRICYCLO-[8.3.0.04,9]TRIDECANE
AMBERLYN SUPER
AMBROXAN
(-)-AMBROXIDE
DODECAHYDROTETRAMETHYLNAPHTHOFURAN
FEMA 3471
1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-,[3aR-(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)]-Naphtho[2
8.alpha.-12-Oxido-13,14,15,16-tetranorlabdane
9aalpha,9bbeta)]-bet
Ambrox
Naphtho[2,1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-,[3aR-(3a.alpha.,5a.beta.,9a.al
naphtho[2,1-b]furan,dodecahydro-3a,6,6,9a-tetramethyl-,[3atheta-(3aalpha,5a
n-Epoxide
[3aR-(3aalpha,5abeta,9aalpha,9bbeta)]-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan
Amberoxan
Ambropur
(-)-AMBROXIDE 99+%
Naphtho2,1-bfuran, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-
(3aR,5aS,9aS,9bR)-Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan
Ambroxane

CAS:

6790-58-5

MF:

C16H28O

MW:

236.39

EINECS:

229-861-2

Product Categories:

Mol File:

6790-58-5.mol

Melting point

74-76 °C (lit.)

alpha

-30 º (c=1% in toluene)

Boiling point 

273.9±8.0 °C(Predicted)

density 

0.939

vapor pressure

0.066Pa at 25℃

FEMA

3471

storage temp.

Sealed in dry,Room Temperature

form

powder to crystaline

color

White to Almost white

Odor

at 1.00 % in dipropylene glycol. ambergris old paper sweet labdanum dry

Odor Type

amber

optical activity

[α]20/D 29°, c = 1 in toluene

Water Solubility

1.88mg/L at 20℃

Description

Ambroxan is a synthetic spice with the special aroma of natural ambergris, and it is recognized as one of the best substitutes for natural ambergris. It is one of the most critical trace components of natural ambergris tincture. Natural ambergris is a precious animal spice. It is a kind of stone in the stomach of sperm whale. It is vomited or excreted on the sea surface by the whale, and it emits a special fragrance in the air for a long time.

Uses

Ambroxide can be used:

To prepare (+)-sclareolide through C?H?oxidation strategy.

As a substrate in C(sp3)-H alkylation/arylation studies of ethers.

As a substrate in the study of ethereal hydrocarbon hydroperoxidation using singlet O2.

Application

Ambroxan has a strong, characteristic ambergris aroma. Used in high-grade perfumes and cosmetic essences, because it is non-irritating to the human body and non-allergic to animals, it is very suitable for fragrances for skin, hair and fabrics. Often used in soaps, talcum powders, creams and shampoos for perfuming and fixing fragrance.

Definition

ChEBI: A diterpenoid derived from sclareol that is responsible for the odour of ambergris (a solid, waxy, flammable substance produced in the digestive system of sperm whales).

Preparation

Ambroxene naturally occurring autoxidation or photooxide of the triterpenoid secreted by sperm whales.
Industrially, High acacia acid was prepared from nerolidol. After acid internal esterification, the racemic Ambroxene was obtained.
Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage. Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol. The resulting compound is dehydrated to form ambroxide.

Synthesis

Perillyl alcohol is used as raw material to synthesize nordrone ether, which is oxidized by KMnO4 in two steps (Switzerland uses ozone oxidation, Russia uses sodium chromate oxidation). That is (1) alkaline oxidation; (2) weak acid oxidation. The oxide is obtained, and then the oxide is soaped, dehydrated and lactonized to obtain ambroxolide.  lactones are reduced to ambroxol with lithium aluminum hydride in ether (or with borane in tetrahydrofuran). D-camphor-β-sulfonic acid is used as a cyclizing agent to cyclize diols to obtain ambrox (foreign cyclizing agents include sulfuric acid, p-toluenesulfonic acid and β-naphthalenesulfonic acid, etc.). 

Raw materials

Tetrahydrofuran-->PARA TOLUENE-->Ozone-->Naphthalene-2-sulfonic acid-->Diborane-->D-CAMPHOR-->DIHYDRO CUMINYL ALCOHOL