59614-85-6

Basic information

• Product Name: (S)-3-METHYLHEPTANOIC ACID
• Synonyms: (S)-3-METHYLHEPTANOIC ACID
• CAS NO: 59614-85-6
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• Mol File: 59614-85-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 234.6℃
• Flash Point: 116.6℃
• Appearance: /
• Density: 0.926
• CAS DataBase Reference: (S)-3-METHYLHEPTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-METHYLHEPTANOIC ACID(59614-85-6)
• EPA Substance Registry System: (S)-3-METHYLHEPTANOIC ACID(59614-85-6)

Safety Data

• Hazardous Substances Data: 59614-85-6(Hazardous Substances Data)

Usage

General Description

(S)-3-Methylheptanoic acid, also known as (S)-3-Methylheptylic acid, is a chemical compound classified as a fatty acid. It is a carboxylic acid with a molecular formula of C8H16O2. (S)-3-METHYLHEPTANOIC ACID is a colorless liquid with a rancid odor and is found naturally in certain foods and beverages. (S)-3-Methylheptanoic acid is used in the production of flavors and fragrances due to its characteristic odor. It is also a precursor in the synthesis of pharmaceuticals and other organic compounds. Additionally, it is used in the manufacturing of plastics, resins, and other industrial products. This chemical is a valuable compound with a wide range of applications.

Synthetic route

3-methylideneheptanoic acid (84817-84-5) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With C38H36IrO2P; hydrogen; caesium carbonate In butan-1-ol at 65℃; under 2280.15 Torr; enantioselective reaction;	99%

(1'S,2'S,3S)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N,3-dimethylheptanamide (913962-59-1) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 6h; Heating;	88%

S-3-methyl-6-heptenoic acid (116370-22-0) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate under 2585.7 Torr; for 2h;	87%

(S)-(4-methyloct-1-ene-1,1-diyl)dibenzene → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol at 20℃; for 6h; pH=8 - 9; Reagent/catalyst; Solvent;	84%

(S)-3-methylheptan-1-ol (61169-84-4, 1070-32-2, 99427-18-6, 111767-94-3) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With potassium permanganate; acetic acid In acetone Ambient temperature;	81%
With hydrogenchloride; Ca(OCl2)2 In tetrachloromethane for 5h;

C32H39NO3 → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 10h;	71%

methyl (S)-3-methyl-5-oxoheptanoate (109622-00-6) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With potassium hydroxide; hydrazinium sulfate In water; diethylene glycol for 18.5h;	61%

(S)-(-)-methyl 3-methylheptanoate (99439-79-9) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

1-bromo-butane (109-65-9) + (S)-1-crotonoyl-2-(1-hydroxy-1-methylethyl)pyrrolidine → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (R)-3-methylheptanoic acid (57403-74-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene from -40 deg C to room temp.; Yield given. Yields of byproduct given;

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-heptan-1-one (108509-68-8) → (-)-(S)-3-methylheptanoic acid (59614-85-6)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran; water for 18h; Ambient temperature; Yield given;

(S)-3-Methyl-heptanoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (81002-23-5) → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (-)-8-phenylmenthol (65253-04-5)

Conditions	Yield
With sodium methylate In methanol; water at 75℃; for 24h;

(5S)-N-[(3R)-methylheptanoyl]-5-triphenylmethoxymethyl-2-pyrrolidinone (105526-90-7) → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (R)-3-methylheptanoic acid (57403-74-4)

Conditions	Yield
With hydrogenchloride; potassium hydroxide 1.) MeOH, reflux, 12 h, 2.) MeOH-water, reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(E)-2-((S)-Benzenesulfinyl)-but-2-enoic acid methyl ester (77727-24-3) → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (R)-3-methylheptanoic acid (57403-74-4)

Conditions	Yield
With ethanol; aluminium amalgam; di-n-butylcopperlithium; water Product distribution; multistep reaction, asymmetric induction;

(S)-3-Methyl-heptanoic acid ((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (88020-53-5) → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (R)-3-methylheptanoic acid (57403-74-4)

Conditions	Yield
With sulfuric acid; acetic acid for 3h; Heating; Yield given;

(S)-3-Methyl-heptanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (96864-22-1) → (-)-(S)-3-methylheptanoic acid (59614-85-6) + (-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7)

Conditions	Yield
With sodium hydroxide In ethanol Heating; Yield given. Yields of byproduct given;

Upstream product

• 109-65-9 1-bromo-butane 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 99439-79-9 (S)-(-)-methyl 3-methylheptanoate 
• 84817-84-5 3-methylideneheptanoic acid 
• 909879-22-7 methyl (R)-5-bromo-4-methylpentanoate 
• 1042351-59-6 C₁₈H₃₁NO 
• 1042351-31-4 1-methoxy-2-(2-methylhexyl)benzene 
• 1042351-26-7 benzyl-[2-(2-methylhexyl)benzyl]amine 
• 909726-04-1 (S)-benzyl[2-(2-methylhexyl)phenyl]amine 
• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 
• 104651-11-8 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-hept-2-en-1-one 
• 175170-59-9 ((S)-3-methyl-hept-6-enyloxymethyl)-benzene 
• 116370-26-4 (4S)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-methylhexanal 
• 116370-20-8 7-(t-butyldimethylsiloxy)-5(S)-methyl-hept-1-ene 

Downstream Products

• 188123-54-8 (1S,2R,6S,7S,8S)-8-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-3-methyl-heptanoyl)-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]decan-4-one 
• 97424-48-1 (S)-1-bromo-2-methylhexane 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 251968-34-0 (3S)-methyl-1-tosyloxyheptane 
• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 

Relevant articles and documents

CuH-Catalyzed Asymmetric Conjugate Reductions of Acyclic Enones

A powerful new reaction has been developed for the asymmetric 1, 4-reduction of prochiral enones (see scheme). The key ingredients in this exceedingly mild and straightforward procedure are catalytic quantities of CuH, a readily available nonracemic phosphane ligand such as that shown, and inexpensive polymethyl-hydrosiloxane (PMHS) as the stoichiometric source of hydride.

Syntheses of (R)- and (S)-3-methylheptanoic acids

Starting from chiral methyl molecules 3 and 4, both derived from (R)-4-methyl-δ-valerolactone, we have accomplished the synthesis of (R) and (S)-3-methylheptanoic acids. Our methods are amendable to the syntheses of a wide variety of chiral 3-methyl alkanoic acids. Both enantiomers of 3-methylheptanoic acid have been synthesized from chiral methyl molecules which were derived from (R)-4-methyl-δ-valerolactone (5). A wide variety of chiral 3-methyl alkanoic acids can also be synthesized by the methods described herein.

Anthracene cycloadducts as highly selective chiral auxiliaries

(Chemical Equation Presented) A new chiral auxiliary was designed and easily prepared from a Diels-Alder cycloadduct of an enantiomerically pure anthracene with maleimide. Excellent diastereoselectivities in Diels-Alder reactions, conjugate additions, and aldol reactions employing these auxiliaries are now reported.