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1856-58-2

(3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one is a complex organic compound characterized by its unique molecular structure. It features a decalin (a type of hydrocarbon) backbone with a naphthalene (a fused ring system) and a furan (a five-membered ring with one oxygen atom) ring fused together. The compound has two methyl groups at the 3 and 8a positions, and a methylidene bridge connecting the decalin and furan rings. This structure classifies it as a tricyclic sesquiterpene, which are a group of natural products derived from plants. The specific stereochemistry indicated by the prefixes (3S,3aR,4aS,8aR,9aR) describes the three-dimensional arrangement of the molecule's atoms, which is crucial for its biological activity and reactivity. (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one is of interest in organic chemistry and may have potential applications in the synthesis of natural products and pharmaceuticals due to its intricate structure and potential biological activity.

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  • 1856-58-2 Structure

  • Basic information

    1. Product Name: (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
    2. Synonyms: Naphtho[2,3-b]furan-2(3H)-one, decahydro-3,8a-methyl-5-methylene-, (3S,3aR,4aS,8aR,9aR)-
    3. CAS NO:1856-58-2
    4. Molecular Formula: C15H22O2
    5. Molecular Weight: 234.334
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1856-58-2.mol

  • Chemical Properties

    1. Melting Point: 171-172 °C
    2. Boiling Point: 354.8°C at 760 mmHg
    3. Flash Point: 148°C
    4. Appearance: N/A
    5. Density: 1.06g/cm3
    6. Vapor Pressure: 3.26E-05mmHg at 25°C
    7. Refractive Index: 1.515
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one(CAS DataBase Reference)
    11. NIST Chemistry Reference: (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one(1856-58-2)
    12. EPA Substance Registry System: (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one(1856-58-2)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1856-58-2(Hazardous Substances Data)

1856-58-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1856-58-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,5 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1856-58:
(6*1)+(5*8)+(4*5)+(3*6)+(2*5)+(1*8)=102
102 % 10 = 2
So 1856-58-2 is a valid CAS Registry Number.

1856-58-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (3S,3aR,4aS,8aR,9aR)-3,8a-dimethyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one

1.2 Other means of identification

Product number -
Other names Dihydroisoalantolactone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1856-58-2 SDS

1856-58-2Relevant articles and documents

Sesquiterpenolides from Inula racemosa and their chemical transformations

Kaur, Ramandeep,Chahal,Bhardwaj, Urvashi

, p. 568 - 570 (2017)

Inula racemosa roots are rich source of sesquiterpene lactones. Soxhlet extraction of roots using chloroform followed by column chromatography on silver nitrate impregnated silica gel led to the isolation of two sesquiterpene lactones namely alantolactone

Isolation, Chemical Transformation, and Antifungal Potential of Sesquiterpene Lactones from Inula Racemosa

Kaur, Ramandeep,Chahal,Urvashi

, p. 207 - 212 (2020/04/17)

The present study reports the isolation of two eudesmanolide type sesquiterpenoid lactones, viz. alantolactone and isoalantolactone, from the roots of Inula racemosa Hook L. and their chemical transformations using various reagents. All the compounds isol

Total Synthesis of Three Eudesman-12,8-olides, (+/-)-Isoalantolactone, (+/-)-Dihydrocallitrisin and (+/-)-Septuplinolide; Structure Revision of Septuplinolide

Tada, Masahiro,Yamada, Hirokazu,Kanamori, Akira,Chiba, Kazuhiro

, p. 239 - 248 (2007/10/02)

Four eudesman-12,8-olides, (+/-)-isoalantolactone, (+/-)-dihydrocallitrisin, (+/-)-septuplinolide and its epimeric eudesmanolide at C-4 were synthesized stereoselectively via the route involving alkylation annulation of 2-methyl-3-furoic acid and oxidation of the furan ring.It was found that the structure of septuplinolide is the C-4 epimer of the reported structure.

Synthesis of Deuterium-Labeled Sesquiterpene Lactones Isolated from Inula helenium L.

Schaeffer, Marcel,Stampf, Jean-Luc,Benezra, Claude

, p. 6106 - 6113 (2007/10/02)

Reduction of the vinyl sulfoxides 9 and 10 derived from isoalantolactone (1) and alantolactone (2) with NaBD4 yielded deuterium-labeled lactones 11 and 12.Amalgam reduction of sulfides 7 and 8 or sulfoxides 9 and 10 gave labeled products but not the expected deuterated lactones 11 and 12.Satisfactory deuteration of alantolactone 2 could be achieved by CF3COOD hydrolysis of (tributylstannyl)alantolactone (23) obtained in four steps from alantolactone 2.

TOTAL SYNTHESIS OF (+/-)-ISOALANTOLACTONE AND (+/-)-DIHYDROCALLITRISIN

Tada, Masahiro

, p. 441 - 444 (2007/10/02)

Two eudesmanolides having opposite stereochemistry of lactone ring each other, (+/-)-isoalantolactone and (+/-)-dihydrocallitrisin were sythesized stereoselectively by a route involving alkylation of 2-methyl-3-furonic acid and oxidation of furan ring.

An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon

Schultz, Arthur G.,Godfrey, Jollie D.

, p. 2414 - 2428 (2007/10/02)

An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphthofuran-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.

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