6790-58-5 Usage
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.
Definition
ChEBI: Ambroxan is 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). It is an organic heterotricyclic compound and a diterpenoid.
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.
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.
General Description
Ambroxide is a terpenoid, which has vast applications in the perfume industry due to its fixative property and odor. Ambergris, which was originally sourced from sperm whale, has been substituted by synthetic ambroxides.
Flammability and Explosibility
Notclassified
Side effects
The most common side effects associated with Ambroxane use include those which are observed among patients developing allergic reactions. These include pruritus, hives, and swelling in the face, lips, tongue, or throat. It is important to immediately seek medical attention upon the development of dangerous adverse allergic reactions like difficulty in breathing, shortness of breath, convulsions, and mood changes.
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.).
Check Digit Verification of cas no
The CAS Registry Mumber 6790-58-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,7,9 and 0 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6790-58:
(6*6)+(5*7)+(4*9)+(3*0)+(2*5)+(1*8)=125
125 % 10 = 5
So 6790-58-5 is a valid CAS Registry Number.
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
6790-58-5Relevant articles and documents
Preparation of two diastereoisomeric decalin synthons and (-)-ambrox
Xie, Yi-Peng,Li, Bo-Gang,Luo, Ying-Gang,Chen, Xiao-Zhen,Zhang, Guo-Lin
, p. 734 - 740 (2008)
Two diastereoisomeric decalins, (2S,4aS,5S,6R)- and (2S,4aS,5R,6R)-5-(2- hydroxyethyl)-1,1,4a,6-tetramethyldecalin-2,6-diol (5 and 6) were prepared from the degradation products of oleanolic acid. Starting from 6, (-)-ambrox (4) was synthesized.
Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol
Zubar, Viktoriia,Lichtenberger, Niels,Schelwies, Mathias,Oeser, Thomas,Hashmi, A. Stephen K.,Schaub, Thomas
, (2021/11/16)
The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.
A SOLID FORM OF (-)-AMBROX FORMED BY A BIOVERVERSION OF HOMOFARNESOL IN THE PRESENCE OF A BIOCATALYST
-
, (2017/11/15)
A solid form of (-)-Ambrox formed by a bioconversion process.
Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction
Alonso, Pedro,Pardo, Pilar,Fontaneda, Raquel,Fa?anás, Francisco J.,Rodríguez, Félix
, p. 13158 - 13163 (2017/09/06)
The synthesis of cyclic alkenyl halides (mainly fluorides, chlorides and bromides) from alkynol or enyne derivatives by an acid-mediated cationic cyclisation reaction is disclosed. This high-yielding, scalable and technically simple method complements and challenges conventional methodologies. This study includes the development of biomimetic cationic cyclisation reactions of polyenyne derivatives to give interesting halogen-containing polycyclic compounds. The application of this reaction in the key step of the synthesis of two terpenes, namely austrodoral and pallescensin A, and the potent odorant 9-epi-Ambrox demonstrates the potential of the reaction for natural product synthesis.