(+/-)-GEOSMIN

Base Information

• Chemical Name: (+/-)-GEOSMIN
• CAS No.: 16423-19-1
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.306
• Mol file: 16423-19-1.mol

Synonyms:4a(2H)-Naphthalenol,octahydro-4,8a-dimethyl-, (4a,4aa,8ab)- (9CI); 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-,(4a,4aa,8ab)-(?à)-; 4aa(2H)-Naphthol, octahydro-4a,8ab-dimethyl-, (?à)- (8CI); (?à)-Geosmin;DL-Geosmin; dl-Geosmin

Chemical Property of (+/-)-GEOSMIN

Chemical Property:

• Vapor Pressure: 0.000928mmHg at 25°C
• Boiling Point: 270°C at 760 mmHg
• PKA: 15.23±0.60(Predicted)
• Flash Point: 11 °C
• PSA: 20.23000
• Density: 0.985g/cm³
• LogP: 3.11780
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

racGeosmin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T,F
• Hazard Codes: Xi,T,F
• Statements: 36-39/23/24/25-23/24/25-11
• Safety Statements: 26-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Geosmin is a major volatile component of beet essence, also determined to be the potent earthy odor contaminant of fish, beans, water. (±)-Geosmin solution is commonly used in the odorant removal/degradation studies in the water and food chemistry. (±)-Geosmin has been used as a standard for GC-MS based analytical techniques. Geosmin has also been used to study its adsorption on activated carbon.

Technology Process of (+/-)-GEOSMIN

There total 18 articles about (+/-)-GEOSMIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

1,4a-dimethyl-trans-3,4,4a,5,6,7,8,8a-otahydronaphthalen-8a-ol (73428-93-0,132087-77-5) → r-1,c-4a-dimethylperhydronaphthalen-t-8a-ol (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; at 100 ℃; for 36h; under 72200.1 Torr;

Reference yield: 72.0%

Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester (125107-10-0,125137-16-8) → (+/-)-Geosmin (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1016/S0040-4039(00)99122-6

Reference yield:

(+/-)-perhydro-7β,8aβ-dihydroxy-1β-methylnaphthalene-4aα-carbaldehyde (126370-56-7) → (+/-)-Geosmin (5173-69-3,5173-70-6,16423-19-1,16452-32-7,19700-21-1,23333-91-7,104873-46-3,132154-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Py*TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1) N₂H₄; 2) KOH; 3) Py*TsOH / 1) 110 deg C, 30 min; 2) 180 deg C, 1 h; 3) MeOH, 60 deg C, 30 min

3: 90 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

4: Zn powder, NaI / 1,2-dimethoxy-ethane / 4 h / 90 - 95 °C

With pyridine; potassium hydroxide; pyridinium p-toluenesulfonate; sodium iodide; hydrazine; zinc; pyridinium p-toluenesulfonate; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1002/hlca.19900730114

upstream raw materials:

trans-8,10-Dimethyl-1⁽⁹⁾-octalin

Methanesulfonic acid (2S,4aR,8R,8aR)-8a-hydroxy-4a,8-dimethyl-decahydro-naphthalen-2-yl ester

1,4a-dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one

Toluene-4-sulfonic acid (1aS,4aR,8aR)-1a,4a-dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-2-yl ester

Downstream raw materials:

markiertes 8ref,10cis-Dimethyl-1(9)-octalin

Refernces

• 1、 Hansson, Lars,Carlson, Rolf. "Synthesis of (+/-)-Geosmin. Part 2. A One-Pot Four-Step Conversion of 1,4a-Dimethyl-1α,8aα-epoxyperhydronaphthalen-2-one into (+/-)-Geosmin". . p. 1042 - 1045. Retrieved 2007/10/02.
• 2、 Ayer,Browne,Fung. "Metabolites of bird's nest fungi. Part VI. The synthesis of (±)cybullol and a new synthesis of (±)geosmin". . p. 3276 - 3282. Retrieved 2007/10/11.