105-21-5

Basic information

• Product Name: 4-Heptanolide
• Synonyms: 4-hydroxyheptanoic;4-Hydroxyheptanoic acid lactone;4-hydroxyheptanoicacidlactone;5-Propyldihydro-2(3H)-furanone;dihydro-5-propyl-2(3h)-furanon;gamma heptalatone;gamma-Propiobutyrolactone;heptan-4-
• CAS NO: 105-21-5
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 203-279-9
• Product Categories: Cosmetics;lactone flavors
• Mol File: 105-21-5.mol

Chemical Properties

• Boiling Point: 61-62 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow liquid
• Density: 0.999 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0827mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 23g/L at 20℃
• BRN: 109569
• CAS DataBase Reference: 4-Heptanolide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Heptanolide(105-21-5)
• EPA Substance Registry System: 4-Heptanolide(105-21-5)

Safety Data

• Hazard Codes: Xi
• Statements: 38-36/38
• Safety Statements: 36-37/39-26
• WGK Germany: 2
• RTECS: LU3697000
• Hazardous Substances Data: 105-21-5(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
4-Heptanolide is used as a flavoring agent in the food industry due to its sweet, lactonic, creamy, coconut, and coumarin taste characteristics. It is commonly found in green tea, asparagus, beer, strawberry, peach, and beef, adding a unique flavor profile to these products.
Used in Cosmetic Industry:
4-Heptanolide is also used as a flavoring agent in the cosmetic industry, where its sweet, coconut-like, caramel, and herbaceous aroma adds a pleasant scent to various products.
Used as a Fragrance Ingredient:
Due to its distinct aroma, 4-Heptanolide is utilized as a fragrance ingredient in the perfumery industry, contributing to the creation of captivating and long-lasting scents.
Taste and Aroma Threshold Values:

Preparation

Obtained in low yields by hydrogenation of ethyl β-furylacrylate; by lactoniation of heptonic acid; also by condensation of methylacrylate butyl alcohol using a catalyst.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 7360, 1977 DOI: 10.1021/ja00464a048

Hazard

A skin irritant.

InChI:InChI=1/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3

Upstream product

• 18776-90-4 (E)-hept-5-enoic acid 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 927-77-5 n-propylmagnesium bromide 
• 924-97-0 4-oxo-heptanoic acid 
• 89-67-8 α-D-glucoheptonic γ-lactone 
• 110-62-3 pentanal 
• 141-82-2 malonic acid 
• 4798-44-1 1-hexene-3-ol 
• 201230-82-2 carbon monoxide 
• 6225-10-1 N-methylpentanamide 
• 111-14-8 oenanthic acid 
• 693-54-9 Decan-2-one 
• 22935-13-3 2-ethyl-1,6-hexanedioic acid 
• 57681-53-5 5-propylfuran-2(5H)-one 

Downstream Products

• 22094-43-5 4-Hydroxy-heptansaeure-hydrazid 
• 31323-51-0 (S)-γ-Propyl-γ-butyrolactone 
• 88270-38-6 (R)-5-propyl-dihydrofuran-2(3H)-one 
• 295796-51-9 3-hydroxymethyl-5-propyl-dihydro-furan-2-one 
• 4469-89-0 4,7-decanediol 
• 36129-37-0 (+/-)-oudenone 
• 97974-62-4 2-Phenylsulfanyl-2-(5-propyl-tetrahydro-furan-2-yl)-cyclopentane-1,3-dione 
• 1243634-78-7 (-)-methyl (1R,2R,3S,5S)-1-propyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1355075-44-3 (S)-(+)-3-(2-propyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide 
• 1243634-65-2 (+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-propyl-1,3-dioxolan-2-yl)pentanoate 
• 1243634-66-3 (S(S),3S)-(+)-N-(p-toluenesulfinyl)-3-amino-5-(2-propyl-1,3-dioxolan-2-yl)pentanal 
• 1243634-68-5 (Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-propyl-1,3-dioxolan-2-yl)-hept-2-enoate 
• 111-14-8 oenanthic acid 
• 106-42-3 para-xylene 

Relevant articles and documents

FACILE OXIDATIVE CYCLIZATION AND CARBONYLATION OF ALLYLIC ALCOHOLS

Palladium chloride catalyzed reaction of primary, secondary, and tertiary allylic alcohols with carbon monoxide and oxygen, hydrochloric acid, and cupric chloride in tetrahydrofuran affords five-membered ring lactones.

On the mode of baker's yeast reduction of C-7 - C-10 2-alken-4-olides

Baker's yeast reduction of lactones 8, a-d proceeds under kinetic resolution to give (S) 11, a-d of low ee values, increasing with the length of the side chain, occurring the double bond saturation in anti fashion on the beta re face, as indicated by the obtainment from 4 and 6 of 5 and 7, respectively.

Organocatalytic stereoselective approach to the total synthesis of (-)-halosaline

A practical and efficient organocatalytic approach to the synthesis of substituted piperidine alkaloids in high enantio- and diastereomeric excess was achieved using proline-catalyzed sequential α-aminoxylation/α- amination reaction and HWE olefination reaction of an aldehyde.

A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols

An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.

Reactions of hydriodic acid with aldonolactones and n-alkanolactones. Interconversions between lactones and iodocarboxylic acids

Aldonolactones containing from four to eight carbon atoms, and lactones of the related monohydroxy-n-alkanoic acids, were subjected to reaction with 57 percent hydriodic acid at 125 deg C.As in the classical studies of Kiliani, the reduction of D-glycero-D-ido-heptono-1,4-lactone yielded mainly γ-heptanolactone.Analogously, the corresponding γ-alkanolactones were obtained as major products from the 1,4-lactones of the D-xylono, D-allono-, and D-erythro-L-talo-octono configuration.Monoiodo-n-alkanoic acids were also formed in admixture with the lactones in all of these reactions.D-Erythrono-1,4-lactone was unique among the aldonolactones in that it led only to an acid, i.e., 3-iodo-n-butanoic acid.The latter was also the product of the non-reductive reaction of hydriodic acid with β-butyrolactone whereas, by contrast, γ-butyrolactone afforded 4-iodobutanoic acid.Among compounds in the five to eight carbon series, it was found that under conditions close to equilibrium the ratio of lactone to iodoacid decreased progressively with the length of the carbon chain; e.g., in the 4 h reactions of γ-valero, γ-capro, γ-heptano,- and γ-octanolactone, the ratios were 2.4, 1.2, 0.2, and 0.1, respectively.An accompanying characteristic of these reactions is a progression in the number of isomeric iodoacids formed.Whereas γ-valerolactone was accompanied by 4-iodopentanoic acid, there were two isomers (4- and 5-) of iodohexanoic acid, three monoiodo- (including 6-iodo-) heptanoic acids, and four (including 7-iodo-) octanoic acids.In all instances, the isomer substituted at the penultimate carbon was major.An interplay of several individual reactions, including ring-opening displacements, eliminations-additions, and rearrangements, as well as a probable influence of entropy changes on the lactone-acid equilibria, appear to account largely for these observations.

Lactonization of Unsaturated Alcohols Catalyzed by Palladium Complexes under Neutral Conditions

Secondary and tertiary allylic alcohols react with carbon monoxide in the presence of catalytic quantities of bis(dibenzylideneacetone)palladium (0) and 1,4-bis(diphenylphosphino)butane affording lactones in 45-92percent isolated yields. α,β-Unsaturated acids are formed by isomerization and carbonylation of primary allylic alcohols. 2-(5H)-Furanones were isolated in yields of 60-80percent when alkynols were employed as substrates for the cyclocarbonylation process.

Samarium(II) Di-iodide Induced Reductive Coupling of α,β-Unsaturated Esters with Carbonyl Compounds Leading to a Facile Synthesis of γ-Lactone

Samarium(II) di-iodide, which is a strong one-electron transfer reducing agent, is effective for the reductive coupling of α,β-unsaturated esters with carbonyl compounds, whereby substituted γ-lactones can easily be prepared in good to excellent yields under very mild conditions.Two mole equiv. of samarium(II) di-iodide to each mole equiv. of starting substrate always give reasonable yields.The presence of an alcohol is essential in the reaction, complex unidentified products being formed in the absence of an alcohol; t-butyl alcohol gave more satisfactory results than methanol and ethanol.The alcohol acts as a proton donor, the use of MeOD leading to a deuteriated γ-lactone.The reaction is applicable to both aliphatic and aromatic ketones or aldehydes, whereas the electrochemical method is limited to aliphatic substrates.The diastereoselectivity is examined in the reaction of 4-t-butylcyclo-hexanone with ethyl acrylate; an anti-isomer is produced predominantly (syn:anti = 1:9) as the result of selective axial attack.The reaction may proceed by a radical mechanism, and reaction may not involve a samarium ester homoenolate.The reaction is extended to the intramolecular reaction of an α,β-unsaturated keto ester (8-oxonon-2-enoate) leading to the ready synthesis of a bicyclic γ-lactone.

3,3-Diethoxypropyl-lithium: A Masked Lithium Propanal Homoenolate in Organic Synthesis

3,3-Diethoxypropyl-lithium is prepared by lithiation of the corresponding chlorinated precursor with lithium naphthalenide at -78 deg C; the reaction of this masked propanal homoenolate with different elctrophilic reagents CO, (CH2)7CO, PhCOMe, PhCH=NPh, PhCONEt2, PhCN, c-C6H11CN, 4-MeC6H4CN> leads to the corresponding mono- and bi-functionalized compounds.In the case of the reaction with aldehydes or ketones the prepared crude products are oxidized with m-chloroperbenzoic acid, yielding directly the γ-substituted butyrolactones.

Reductive Coupling of Ketones or Aldehydes with Electron-deficient Alkenes Promoted by Samarium Di-iodide

Samarium di-iodide is an efficient reagent for the reductive coupling of ketones or aldehydes and electron-deficient alkenes, whereby γ-lactones can be prepared in good yields from ethyl acrylate.

Oxonium Ion Elektrophiles: Synthesis of the Hypotensive Oudenone.

The hypotensive oudenone (1) has been synthesized through the intermediacy of oxonium ion 4.Acid-catalyzed C-alkylation of 1,3-cyclopentanedione (3) with 5-propyltetrahydro-2-furanol (6b) afforded dihydrooudenone 2b.In contrast, alkylation of 3 with 2-chloro-5-propyltetrahydrofuran (7b) was unsuccessful.Unsaturation was introduced into 2b by treatment with N-(phenylthio)succinimide to produce 10 followed by oxidation to the corresponding sulfoxide and elimination of phenylsulfenic acid, which produced oudenone(1).