564-20-5

Basic information

• Product Name: Sclareolide
• Synonyms: SCLAREOLIDE;1-b]furan-2(1H)-one,decahydro-3a,6,6,9a-tetramethyl-,[3aR-(3a.alpha.,5a.beta.,9a.alpha.,9b.beta.)Naphtho[2;1-b]furan-2(1h)-one,decahydro-3a,6,6,9a-tetramethyl-naphtho[[3atheta-(3a;5abeta,9aalpha,9bbeta)]-alph;Decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one;Norambrienolide;[3aR-(3aalpha,5abeta,9aalpha,9bbeta)]Decahydro-3a,6,6,9a-tetramethylnaphth[2,1-b]furan-2(1H)-one;(3AR)-(+)-SCLAREOLIDE
• CAS NO: 564-20-5
• Molecular Formula: C16H26O2
• Molecular Weight: 250.38
• EINECS: 209-269-0
• Product Categories: Miscellaneous Natural Products;Natural Plant Extract;Flavors & Fragrances;Chiral Building Blocks;Furans;Heterocyclic Building Blocks;Flavors and Fragrances;Inhibitors
• Mol File: 564-20-5.mol
• Article Data: 64

Chemical Properties

• Melting Point: 124-126 °C(lit.)
• Boiling Point: 321.4 °C at 760 mmHg
• Flash Point: 132.4 °C
• Appearance: off-white to white crystal powder
• Density: 1.009 g/cm³
• Vapor Pressure: 0.000299mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility: 10mg/L at 25℃
• CAS DataBase Reference: Sclareolide(CAS DataBase Reference)
• NIST Chemistry Reference: Sclareolide(564-20-5)
• EPA Substance Registry System: Sclareolide(564-20-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• Hazardous Substances Data: 564-20-5(Hazardous Substances Data)

Usage

Chemical Properties

Sclareolide has a musky, wood odor.

Occurrence

Reported present in clary sage bush (Salvia sclarea)

Uses

Different sources of media describe the Uses of 564-20-5 differently. You can refer to the following data:
1. Sclareolide is found in Salvia yosgadensis and is a close analog of sclareol, an antifungal diterpene.
2. antimicrobial
3. sclareolide is a fragrancing ingredient, it can help mask formulation odors. It is synthetically manufactured.

Preparation

Sclareol, isolated from clary sage by solvent extraction, can be efficiently oxidized by the microorganism Cryptococcus albidus to sclareolide.

General Description

Sclareolide is a diterpenoid compound mainly used in the perfume industry for its amber like odor.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1

Upstream product

• 39850-84-5 Acetic acid 1-[2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-decahydro-naphthalen-1-yl)-ethyl]-1-methyl-allyl ester 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 67-66-3 chloroform 
• 10028-15-6 ozone 
• 162599-53-3 14,15-dinor-8α,12-epoxy-13-labdanone 
• 473-03-0 Ambrein 
• 103476-92-2 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-ol 
• 145511-21-3 2-((3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)propan-2-ol 
• 80183-39-7 (3Z,7E)-4,8,12-trimethyltrideca-3,7,11-trienoic acid 
• 64-18-6 formic acid 
• 876503-21-8 (+/-)-4-methyl-6-(2,6,6-trimethyl-cyclohex-2-enyl)-hex-3ξ-enoic acid ethyl ester 
• 84518-22-9 2‐methyl‐4‐(2,6,6‐trimethylcyclohex‐1‐en‐1‐yl)butanal 
• 148700-17-8 (+/-)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-2t-enoic acid 

Downstream Products

• 10207-83-7 (+/-)-13,14,15,16-Tetranor-5β-labdane-8β,12-diol 
• 10207-83-7 (+/-)-13,14,15,16-Tetranor-5β,9β-labdane-8β,12-diol 
• 564-20-5 (+/-)-5β,8α-Sclareolide 
• 3738-00-9 (±)-ambrox 
• 564-20-5 norisoambreinolide 
• 3738-00-9 (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan 
• 6790-58-5 (-)-ambroxide 
• 564-20-5 (3aR)-(+)-sclareolide 
• 335193-14-1 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-hydroxy-2,5,5,8a-tetramethyl-1-naphthaleneethanol 
• 53163-43-2 8-drimanol 
• 29064-99-1 2-oxosclareolide 
• 292643-80-2 (+)-1-oxo-sclareolide 
• 74483-92-4 (+)-3-oxo-sclareolide 
• 1422446-22-7 C₁₆H₂₆O₃ 

Relevant articles and documents

Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds

We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.

Flavin Nitroalkane Oxidase Mimics Compatibility with NOx/TEMPO Catalysis: Aerobic Oxidization of Alcohols, Diols, and Ethers

Biomimetic flavin organocatalysts oxidize nitromethane to formaldehyde and NOx - providing a relatively nontoxic, noncaustic, and inexpensive source for catalytic NO2 for aerobic TEMPO oxidations of alcohols, diols, and ethers. Alcohols were oxidized to aldehydes or ketones, cyclic ethers to esters, and terminal diols to lactones. In situ trapping of NOx and formaldehyde suggest an oxidative Nef process reminiscent of flavoprotein nitroalkane oxidase reactivity, which is achieved by relatively stable 1,10-bridged flavins. The metal-free flavin/NOx/TEMPO catalytic cycles are uniquely compatible, especially compared to other Nef and NOx-generating processes, and reveal selectivity over flavin-catalyzed sulfoxide formation. Aliphatic ethers were oxidized by this method, as demonstrated by the conversion of (-)-ambroxide to (+)-sclareolide.

METHOD FOR PRODUCING SCLAREOLIDE

A method for producing slcareolide comprising the following steps: (a) providing sclareol as starter material; (b) contacting the starter material sclareol with ozone in air or oxygen as the sole oxidant in an acidic medium.