alpha-Angelica lactone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    591-12-8

    Molecular formula
    C5H6O2

    SMILES
    CC1=CCC(=O)O1

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1430.0

  • Odor profile

    Sweet 72.36%
    Coumarinic 70.73%
    Coconut 64.8%
    Nutty 64.18%
    Herbal 52.69%
    Tobacco 51.24%
    Caramellic 50.91%
    Spicy 47.32%
    Hay 44.85%
    Buttery 44.07%

    Scent© AI

  • Properties

    XLogP3-AA
    0.6

    Molecular weight
    98.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    160°C

    Flash point est.
    55.66 ˚C

  • Synonyms

    • alpha-Angelica lactone
    • 591-12-8
    • alpha-Angelicalactone
    • 5-Methylfuran-2(3H)-one
    • 5-Methyl-2(3H)-furanone
    • 5-methyl-3H-furan-2-one
    • 2(3H)-FURANONE, 5-METHYL-
    • 4-Hydroxypent-3-enoic acid lactone
    • delta(2)-Angelica lactone
    • 4-Hydroxy-3-pentenoic acid gamma-lactone
    • .alpha.-Angelica lactone
    • gamma-Methyl-beta,gamma-crotonolactone
    • alpha-Angelicalacton
    • delta(sup 2)-Angelica lactone
    • FEMA No. 3293
    • CCRIS 3594
    • .beta.,.gamma.-Angelica lactone
    • NSC 654
    • a-angelicalactone
    • beta,gamma-Angelica lactone
    • a-Angelica lactone
    • EINECS 209-701-8
    • .DELTA.2-Angelica lactone
    • UNII-29CRF6L9C5
    • .delta.(2)-Angelica lactone
    • BRN 0108394
    • 29CRF6L9C5
    • DTXSID7047693
    • CHEBI:36433
    • AI3-04326
    • NSC-654
    • .alpha.-angelicalactone
    • alpha(beta,gamma or delta2)-Angelica lactone
    • 3-Pentenoic acid, 4-hydroxy-, gamma-lactone
    • MFCD00005375
    • 4-Methyl-2(3H)-furanone
    • PENT-3-EN-4-OLIDE
    • NSC654
    • 4-Hydroxy-3-pentenoic acid .gamma.-lactone
    • .GAMMA.-ANGELICA LACTONE
    • DTXCID5027693
    • 3-Pentenoic acid, 4-hydroxy-, .gamma.-lactone
    • 2,3-Dihydro-5-methyl-2-furanone
    • 2-Oxo-5-methyl-2,3-dihydrofuran
    • 5-17-09-00120 (Beilstein Handbook Reference)
    • .ALPHA.-ANGELICA LACTONE [FHFI]
    • 2,3-DIHYDRO-5-METHYLFURAN-2-ONE
    • 5-METHYL-2,3-DIHYDRO-2-FURANONE
    • ANGELICA LACTONE .ALPHA.-FORM [MI]
    • .gamma.-Methyl-.beta.,.gamma.-crotonolactone
    • Penten-3-oic acid, 4-hydroxy-, .gamma.-lactone
    • 4-HYDROXY-3-PENTENOIC ACID.GAMMA.-LACTONE
    • 4-Hydroxy-3-pentenoic acid ?-lactone
    • 3-Penten-4-olide
    • a-angelicalacton
    • |A-Angelicalactone
    • ?-Angelica lactone
    • b,g-Angelica lactone
    • alpha -Angelica lactone
    • g-Methyl-b,g-crotonolactone
    • WLN: T5OV CHJ E1
    • GAMMA-ANGELICA LACTONE
    • alpha-Angelica lactone, 98%
    • CHEMBL478640
    • 4-Hydroxypent-3-enoate lactone
    • 4-Hydroxy-3-pentenoate g-lactone
    • ANGELICA LACTONE ALPHA-FORM
    • 5-methyl-2,3-dihydrofuran-2-one
    • alpha-Angelica lactone, 98%, FG
    • 3-Pentenoic acid, .gamma.-lactone
    • 4-Hydroxy-3-pentenoate I3-lactone
    • HY-N0548
    • Tox21_303997
    • 4-Hydroxy-3-pentenoate gamma-lactone
    • AKOS015866998
    • SB60998
    • 4-Hydroxy-3-pentenoic acid I3-lactone
    • NCGC00356975-01
    • CAS-591-12-8
    • FA106390
    • PENTEN-3-OIC ACID, GAMMA-LACTONE
    • SY049831
    • a-Angelica lactone, =90% sum of isomers
    • alpha-Angelica lactone, analytical standard
    • DB-053321
    • A1090
    • CS-0009076
    • NS00012893
    • EN300-90517
    • 4-HYDROXY-3-PENTENOIC ACIDGAMMA-LACTONE
    • D88375
    • .alpha.(.beta.,.gamma. or .DELTA.2)-Angelica lactone
    • 3-PENTENOIC ACID,4-HYDROXY,LACTONE ALPHA-ANGELICA-LACTONE

  • Applications

    α-Angelica lactone (CAS 591-12-8) is an unsaturated γ-lactone with a characteristic sweet, caramel-like odor that finds broad use in the flavor industry to impart honey, toasted sugar and ripe fruit nuances, in perfumery to add warm gourmand depth, in e-cigarette liquids and beverages as a natural flavor modifier, and it serves as a versatile intermediate for the synthesis of high-value furanone derivatives; because its γ-lactone ring readily undergoes nucleophilic opening, the compound is an important building block in pharmaceuticals for anti-inflammatory and antimicrobial agents, in agrochemistry for plant-growth regulators, in specialty chemicals for producing biodegradable polymer monomers, eco-friendly paint thinners, recyclable solvents, and it is being explored as a high-energy carrier, an additive in organic battery electrolytes, and a bio-labeling probe owing to its isotopic tagging capability.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 474.88
    methanol 655.15
    isopropanol 393.39
    water 102.57
    ethyl acetate 211.18
    n-propanol 314.83
    acetone 521.52
    n-butanol 231.11
    acetonitrile 467.49
    DMF 1031.04
    toluene 70.46
    isobutanol 219.39
    1,4-dioxane 510.46
    methyl acetate 326.12
    THF 448.02
    2-butanone 293.68
    n-pentanol 138.1
    sec-butanol 306.85
    n-hexane 10.73
    ethylene glycol 275.73
    NMP 688.89
    cyclohexane 9.03
    DMSO 643.76
    n-butyl acetate 43.91
    n-octanol 67.7
    chloroform 467.88
    n-propyl acetate 71.1
    acetic acid 593.57
    dichloromethane 388.8
    cyclohexanone 208.5
    propylene glycol 347.54
    isopropyl acetate 102.1
    DMAc 893.72
    2-ethoxyethanol 329.37
    isopentanol 153.79
    n-heptane 5.16
    ethyl formate 158.76
    1,2-dichloroethane 173.66
    n-hexanol 74.8
    2-methoxyethanol 681.04
    isobutyl acetate 43.58
    tetrachloromethane 48.25
    n-pentyl acetate 46.37
    transcutol 531.51
    n-heptanol 45.34
    ethylbenzene 36.56
    MIBK 97.85
    2-propoxyethanol 207.49
    tert-butanol 327.16
    MTBE 174.17
    2-butoxyethanol 116.14
    propionic acid 332.49
    o-xylene 56.67
    formic acid 432.84
    diethyl ether 172.92
    m-xylene 50.92
    p-xylene 56.51
    chlorobenzene 101.15
    dimethyl carbonate 162.79
    n-octane 3.37
    formamide 645.72
    cyclopentanone 337.73
    2-pentanone 181.91
    anisole 159.34
    cyclopentyl methyl ether 168.95
    gamma-butyrolactone 439.78
    1-methoxy-2-propanol 477.33
    pyridine 308.91
    3-pentanone 131.16
    furfural 432.58
    n-dodecane 4.84
    diethylene glycol 239.73
    diisopropyl ether 35.9
    tert-amyl alcohol 266.65
    acetylacetone 238.29
    n-hexadecane 5.25
    acetophenone 126.42
    methyl propionate 235.44
    isopentyl acetate 44.89
    trichloroethylene 392.03
    n-nonanol 59.97
    cyclohexanol 152.22
    benzyl alcohol 137.32
    2-ethylhexanol 38.08
    isooctanol 36.48
    dipropyl ether 36.29
    1,2-dichlorobenzene 91.04
    ethyl lactate 78.47
    propylene carbonate 196.06
    n-methylformamide 559.54
    2-pentanol 147.06
    n-pentane 11.17
    1-propoxy-2-propanol 113.67
    1-methoxy-2-propyl acetate 95.98
    2-(2-methoxypropoxy) propanol 152.72
    mesitylene 27.01
    ε-caprolactone 194.24
    p-cymene 18.68
    epichlorohydrin 397.21
    1,1,1-trichloroethane 181.53
    2-aminoethanol 399.92
    morpholine-4-carbaldehyde 607.67
    sulfolane 404.13
    2,2,4-trimethylpentane 8.26
    2-methyltetrahydrofuran 308.69
    n-hexyl acetate 90.39
    isooctane 5.16
    2-(2-butoxyethoxy)ethanol 186.71
    sec-butyl acetate 54.55
    tert-butyl acetate 102.2
    decalin 9.14
    glycerin 412.57
    diglyme 297.99
    acrylic acid 351.32
    isopropyl myristate 40.89
    n-butyric acid 223.59
    acetyl acetate 134.66
    di(2-ethylhexyl) phthalate 47.68
    ethyl propionate 86.8
    nitromethane 962.82
    1,2-diethoxyethane 94.08
    benzonitrile 133.31
    trioctyl phosphate 31.24
    1-bromopropane 93.5
    gamma-valerolactone 494.28
    n-decanol 44.0
    triethyl phosphate 36.07
    4-methyl-2-pentanol 70.46
    propionitrile 198.65
    vinylene carbonate 200.26
    1,1,2-trichlorotrifluoroethane 347.58
    DMS 108.06
    cumene 28.19
    2-octanol 37.38
    2-hexanone 89.18
    octyl acetate 54.52
    limonene 25.43
    1,2-dimethoxyethane 386.42
    ethyl orthosilicate 33.21
    tributyl phosphate 38.35
    diacetone alcohol 180.69
    N,N-dimethylaniline 107.79
    acrylonitrile 303.72
    aniline 176.28
    1,3-propanediol 376.67
    bromobenzene 83.98
    dibromomethane 195.73
    1,1,2,2-tetrachloroethane 285.88
    2-methyl-cyclohexyl acetate 46.56
    tetrabutyl urea 55.18
    diisobutyl methanol 24.86
    2-phenylethanol 79.62
    styrene 49.82
    dioctyl adipate 63.87
    dimethyl sulfate 268.67
    ethyl butyrate 45.09
    methyl lactate 193.15
    butyl lactate 56.96
    diethyl carbonate 40.01
    propanediol butyl ether 156.13
    triethyl orthoformate 38.12
    p-tert-butyltoluene 19.64
    methyl 4-tert-butylbenzoate 102.71
    morpholine 580.26
    tert-butylamine 160.38
    n-dodecanol 33.12
    dimethoxymethane 427.03
    ethylene carbonate 144.92
    cyrene 155.39
    2-ethoxyethyl acetate 89.58
    2-ethylhexyl acetate 33.49
    1,2,4-trichlorobenzene 132.38
    4-methylpyridine 305.3
    dibutyl ether 47.74
    2,6-dimethyl-4-heptanol 24.86
    DEF 248.87
    dimethyl isosorbide 183.86
    tetrachloroethylene 160.04
    eugenol 114.09
    triacetin 129.96
    span 80 114.66
    1,4-butanediol 150.5
    1,1-dichloroethane 244.28
    2-methyl-1-pentanol 109.82
    methyl formate 375.73
    2-methyl-1-butanol 173.03
    n-decane 7.1
    butyronitrile 160.24
    3,7-dimethyl-1-octanol 57.74
    1-chlorooctane 29.09
    1-chlorotetradecane 14.17
    n-nonane 6.33
    undecane 5.67
    tert-butylcyclohexane 9.39
    cyclooctane 3.26
    cyclopentanol 218.06
    tetrahydropyran 246.26
    tert-amyl methyl ether 130.52
    2,5,8-trioxanonane 237.65
    1-hexene 38.21
    2-isopropoxyethanol 181.48
    2,2,2-trifluoroethanol 258.6
    methyl butyrate 110.14

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Tamarind 1 dried fruit Tamarindus indica L., fam. Leguminosae 6.24%
Averrhoa bilimbi fruit (Malaysia) Averrhoa bilimbi L., fam. Oxalidaceae 1.1%
Tamarind 3 fruit Tamarindus indica L., fam. Leguminosae 1.6%
Chicory root, roasted 1b 68650-43-1 Cichorium intybus L., fam. Asteraceae (Compositae) 0.15%