Andrographolide

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  • Identifiers

    CAS number
    5508-58-7

    Molecular formula
    C20H30O5

    SMILES
    C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Woody 53.82%
    Spicy 37.98%
    Sweet 36.96%
    Odorless 32.82%
    Mint 25.68%
    Balsamic 25.39%
    Amber 24.49%
    Warm 23.95%
    Dry 23.56%
    Cedar 21.75%

     

    Flavor
    Bitter 79.57%
    Cedarleaf 22.46%
    Sweet-like 20.83%
    Ripe apricot 20.44%
    Lovage 20.2%
    Red fruit 20.08%
    Parsley 20.07%
    Leaves 20.0%
    Patchouli 19.39%
    Ethyl benzoate 19.35%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    6.91 (neutral)

    Molecular weight
    350.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very fast

    Boiling point est.
    589°C

    Flash point

    • 221.78 ˚C est.

  • Synonyms

    • Andrographolide
    • 5508-58-7
    • HMPL004
    • DTXSID3045980
    • CHEBI:65408
    • 410105JHGR
    • NSC-383468
    • DTXCID1025980
    • 3alpha,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid gamma-Lactone
    • (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
    • 3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one
    • (3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
    • 2(3H)-FURANONE, 3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-, (3E,4S)-
    • 2(3H)-Furanone, 3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-, (1R-(1-alpha(E(S*)),4a-beta,5-alpha,6-alpha,8a-alpha))-
    • 2(3H)-Furanone, 3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-, (3E,4S)-
    • (3E,4S)-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)ethylidene)-4-hydroxyoxolan-2-one
    • (3E,4S)-4-hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one
    • RefChem:5554
    • (1R-(1-alpha(E(S)),4a-beta,5alpha,6alpha,8a-alpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone
    • 226-852-5
    • (S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one
    • Andropanolide
    • MFCD07778082
    • (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one
    • (1R-(1-alpha(E(S)),4abeta,5alpha,6alpha,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone
    • (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-decalin-1-yl]ethylidene]-4-hydroxy-tetrahydrofuran-2-one
    • UNII-410105JHGR
    • NSC383468
    • NCGC00095597-01
    • 14-andrographolide
    • (3E,4S)-3-(2-((1R,4AS,5R,6R,8AS)-DECAHYDRO-6-HYDROXY-5-(HYDROXYMETHYL)-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYLIDENE)DIHYDRO-4-HYDROXY-2(3H)-FURANONE
    • (3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
    • 869807-57-8
    • Andrographolide CRS
    • EINECS 226-852-5
    • NSC 383468
    • Andrographiside aglycon
    • Andrographolide, 98%
    • Andrographolide (Standard)
    • Andrographolide Impurity 3
    • ANDROGRAPHOLIDE [MI]
    • BIDD:ER0530
    • CHEMBL186141
    • GTPL9675
    • HMPL-004
    • MEGxp0_000978
    • orb1304874
    • ANDROGRAPHOLIDE [USP-RS]
    • ANDROGRAPHOLIDE [WHO-DD]
    • SCHEMBL12056309
    • ACon1_002113
    • HY-N0191R
    • Andrographolide, analytical standard
    • HY-N0191
    • Tox21_111508
    • BDBM50084419
    • MSK157171
    • AKOS015920075
    • CCG-208428
    • CS-3334
    • DB05767
    • EBC-332046
    • FA17902
    • NCGC00179817-01
    • NCGC00179817-02
    • AS-13637
    • CAS-5508-58-7
    • A2459
    • NS00018311
    • C20214
    • 508A587
    • F078895
    • Q4759444
    • BRD-K89282837-001-01-0
    • ANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]
    • Andrographolide, United States Pharmacopeia (USP) Reference Standard
    • ent-(3|A,12E,14R)-3,14,19-Trihydroxy-8(17),12-labdadien-16,15-olide
    • (3E,4S)-4-Hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}oxolan-2-one
    • 3.ALPHA.,14,15,18-TETRAHYDROXY-5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),12-DIEN-16-OIC ACID .GAMMA.-LACTONE
    • Andrographolide

  • Applications

    Andrographolide, CAS 5508-58-7, is a natural diterpenoid from Andrographis paniculata used as a lead scaffold in pharmaceutical and medicinal chemistry research, and it is investigated as a bioactive compound in studies of inflammatory and antiviral activity; it also serves as an analytical reference standard in HPLC methods and appears as a component of botanical extracts used in cosmetics and personal care; in agricultural research it is evaluated for bioactivity relevant to crop protection; and it can function as an intermediate or starting material for the synthesis of natural product derivatives in industrial chemical manufacturing.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 95.88
    methanol 154.02
    isopropanol 56.54
    water 0.23
    ethyl acetate 58.47
    n-propanol 84.47
    acetone 77.65
    n-butanol 61.47
    acetonitrile 26.44
    DMF 286.03
    toluene 18.68
    isobutanol 34.95
    1,4-dioxane 121.39
    methyl acetate 40.12
    THF 415.61
    2-butanone 56.14
    n-pentanol 17.19
    sec-butanol 27.63
    n-hexane 0.32
    ethylene glycol 25.55
    NMP 115.83
    cyclohexane 0.94
    DMSO 321.59
    n-butyl acetate 22.97
    n-octanol 7.05
    chloroform 133.76
    n-propyl acetate 18.7
    acetic acid 122.53
    dichloromethane 88.68
    cyclohexanone 74.48
    propylene glycol 35.38
    isopropyl acetate 43.54
    DMAc 166.55
    2-ethoxyethanol 100.5
    isopentanol 35.54
    n-heptane 0.36
    ethyl formate 35.73
    1,2-dichloroethane 57.39
    n-hexanol 22.7
    2-methoxyethanol 279.44
    isobutyl acetate 10.13
    tetrachloromethane 10.74
    n-pentyl acetate 18.98
    transcutol 254.44
    n-heptanol 13.23
    ethylbenzene 4.88
    MIBK 37.95
    2-propoxyethanol 130.48
    tert-butanol 47.15
    MTBE 21.35
    2-butoxyethanol 67.16
    propionic acid 42.99
    o-xylene 8.99
    formic acid 100.68
    diethyl ether 34.96
    m-xylene 12.39
    p-xylene 4.61
    chlorobenzene 23.29
    dimethyl carbonate 55.95
    n-octane 0.15
    formamide 153.51
    cyclopentanone 136.12
    2-pentanone 61.24
    anisole 28.97
    cyclopentyl methyl ether 60.76
    gamma-butyrolactone 148.56
    1-methoxy-2-propanol 225.95
    pyridine 79.56
    3-pentanone 32.53
    furfural 125.33
    n-dodecane 0.1
    diethylene glycol 117.44
    diisopropyl ether 6.54
    tert-amyl alcohol 25.1
    acetylacetone 91.77
    n-hexadecane 0.12
    acetophenone 30.08
    methyl propionate 59.28
    isopentyl acetate 23.64
    trichloroethylene 149.67
    n-nonanol 7.48
    cyclohexanol 26.66
    benzyl alcohol 34.01
    2-ethylhexanol 7.8
    isooctanol 9.66
    dipropyl ether 10.63
    1,2-dichlorobenzene 21.92
    ethyl lactate 24.46
    propylene carbonate 56.56
    n-methylformamide 162.61
    2-pentanol 22.37
    n-pentane 0.69
    1-propoxy-2-propanol 66.48
    1-methoxy-2-propyl acetate 71.98
    2-(2-methoxypropoxy) propanol 51.45
    mesitylene 5.68
    ε-caprolactone 70.95
    p-cymene 3.78
    epichlorohydrin 232.36
    1,1,1-trichloroethane 35.23
    2-aminoethanol 73.17
    morpholine-4-carbaldehyde 168.97
    sulfolane 186.86
    2,2,4-trimethylpentane 0.41
    2-methyltetrahydrofuran 77.33
    n-hexyl acetate 19.84
    isooctane 0.44
    2-(2-butoxyethoxy)ethanol 81.73
    sec-butyl acetate 13.32
    tert-butyl acetate 47.47
    decalin 0.42
    glycerin 89.58
    diglyme 169.02
    acrylic acid 51.68
    isopropyl myristate 5.66
    n-butyric acid 81.04
    acetyl acetate 44.45
    di(2-ethylhexyl) phthalate 11.86
    ethyl propionate 22.65
    nitromethane 185.35
    1,2-diethoxyethane 31.59
    benzonitrile 23.33
    trioctyl phosphate 7.74
    1-bromopropane 17.0
    gamma-valerolactone 215.26
    n-decanol 4.17
    triethyl phosphate 12.06
    4-methyl-2-pentanol 13.95
    propionitrile 27.78
    vinylene carbonate 57.75
    1,1,2-trichlorotrifluoroethane 188.58
    DMS 28.3
    cumene 3.11
    2-octanol 5.27
    2-hexanone 16.07
    octyl acetate 8.5
    limonene 4.83
    1,2-dimethoxyethane 113.53
    ethyl orthosilicate 11.0
    tributyl phosphate 7.94
    diacetone alcohol 78.16
    N,N-dimethylaniline 15.01
    acrylonitrile 47.47
    aniline 43.71
    1,3-propanediol 118.43
    bromobenzene 18.46
    dibromomethane 43.39
    1,1,2,2-tetrachloroethane 108.95
    2-methyl-cyclohexyl acetate 15.67
    tetrabutyl urea 10.82
    diisobutyl methanol 5.49
    2-phenylethanol 37.41
    styrene 5.98
    dioctyl adipate 12.57
    dimethyl sulfate 98.21
    ethyl butyrate 18.79
    methyl lactate 71.29
    butyl lactate 28.35
    diethyl carbonate 13.18
    propanediol butyl ether 47.98
    triethyl orthoformate 16.93
    p-tert-butyltoluene 3.96
    methyl 4-tert-butylbenzoate 38.25
    morpholine 187.68
    tert-butylamine 13.33
    n-dodecanol 2.3
    dimethoxymethane 268.45
    ethylene carbonate 48.64
    cyrene 54.7
    2-ethoxyethyl acetate 50.24
    2-ethylhexyl acetate 13.81
    1,2,4-trichlorobenzene 30.96
    4-methylpyridine 54.11
    dibutyl ether 5.04
    2,6-dimethyl-4-heptanol 5.49
    DEF 64.07
    dimethyl isosorbide 91.44
    tetrachloroethylene 64.46
    eugenol 44.78
    triacetin 35.48
    span 80 37.46
    1,4-butanediol 24.01
    1,1-dichloroethane 42.07
    2-methyl-1-pentanol 12.21
    methyl formate 98.87
    2-methyl-1-butanol 27.55
    n-decane 0.25
    butyronitrile 25.7
    3,7-dimethyl-1-octanol 6.94
    1-chlorooctane 2.25
    1-chlorotetradecane 0.55
    n-nonane 0.21
    undecane 0.15
    tert-butylcyclohexane 0.39
    cyclooctane 0.36
    cyclopentanol 41.18
    tetrahydropyran 71.29
    tert-amyl methyl ether 15.77
    2,5,8-trioxanonane 93.01
    1-hexene 1.8
    2-isopropoxyethanol 44.77
    2,2,2-trifluoroethanol 56.88
    methyl butyrate 27.62

    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