Barbaloin

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  • Identifiers

    CAS number
    1415-73-2

    Molecular formula
    C21H22O9

    SMILES
    C1=CC2=C(C(=C1)O)C(=O)C3=C([C@H]2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C(C=C3O)CO

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.72%
    Sweet 36.29%
    Vanilla 35.01%
    Phenolic 27.63%
    Bitter 23.63%
    Milky 22.09%
    Balsamic 20.99%
    Creamy 19.82%
    Spicy 19.4%
    Savory 18.3%

     

    Flavor
    Bitter 85.85%
    Odorless 33.96%
    Bland 29.39%
    Sweet-like 26.02%
    Cedarleaf 20.57%
    Lovage 19.38%
    Nitrile 19.26%
    Parsley 19.15%
    Very mild 18.73%
    Orange flower 18.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    6.74 (neutral)

    Molecular weight
    418.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3304°C

    Flash point

    • 335.17 ˚C est.

  • Synonyms

    • Barbaloin
    • Aloin A
    • 1415-73-2
    • CHEBI:2991
    • DTXSID0045967
    • 648RW354S9
    • DTXCID8025967
    • NSC-407305
    • (1S)-1,5-anhydro-1-[(9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
    • (1S)-1,5-anhydro-1-((9S)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl)-D-glucitol
    • RefChem:27143
    • Barbaloin A
    • (S)-1,8-dihydroxy-3-(hydroxymethyl)-10-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)anthracen-9(10H)-one
    • 9(10H)-Anthracenone, 10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-
    • CHEMBL2103763
    • MFCD00151160
    • 1,8-Dihydroxy-3-hydroxymethyl-10-(6-hydroxymethyl-3,4,5-trihydroxy-2-pyranyl)anthrone
    • Aloin [BAN]
    • 5133-19-7
    • (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
    • (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
    • (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-10H-anthracen-9-one
    • Aloin, from Curacao aloe, ~50%
    • UNII-648RW354S9
    • 10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
    • Barbaloin; Aloin
    • 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-
    • Aloin (Standard)
    • NCGC00183867-01
    • Aloin (Barbaloin)
    • EINECS 215-808-0
    • NSC 227189
    • NSC 631263
    • Aloin, analytical standard
    • ALOIN A [MI]
    • DSSTox_CID_25967
    • DSSTox_RID_82951
    • DSSTox_GSID_48755
    • orb1310868
    • SCHEMBL14837254
    • SCHEMBL29386028
    • SCHEMBL29626884
    • HY-N0123R
    • 1,8-Dihydroxy-10-(beta-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
    • AFHJQYHRLPMKHU-OSYMLPPYSA-N
    • HY-N0123
    • MSK40341
    • Tox21_111495
    • Tox21_113216
    • BDBM50598137
    • EBC-98040
    • s2375
    • AKOS022168218
    • CCG-268870
    • CS-3707
    • MA76226
    • NSC 758464
    • (R)-10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one
    • 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (S)-
    • NCGC00183867-02
    • NCGC00183867-06
    • TS-07631
    • CAS-1415-73-2
    • CAS-8015-61-0
    • NS00066971
    • H10347
    • 415B732
    • Q413888
    • Aloin, from Aloe barbadensis Miller leaves, >=97%
    • BRD-K02074536-001-01-9
    • Aloin, United States Pharmacopeia (USP) Reference Standard
    • (10S)-10-?-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-10H-anthracen-9-one
    • 10-.BETA.-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone-, 10(S)-
    • 10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone,(R)-
    • 9(10H)-Anthracenone, 10-|A-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)-
    • (10S)-10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE
    • 1415-73-2

  • Applications

    Barbaloin is a hydroxyanthraquinone glycoside occurring in Aloe species; in industry it is typically treated as an intermediate and botanical source for hydroxyanthraquinone derivatives such as aloe-emodin and emodin, underpinning its use in cosmetics and personal care as colorants or functional ingredients; in pharmaceutical research it serves as a starting material for synthesis and SAR studies; in the industrial dye/pigment sector it acts as a precursor for anthraquinone-based dyes; it is also used in research settings for isolation and purification workflows and for process development from natural sources.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 7.89
    methanol 25.38
    isopropanol 1.53
    water 0.66
    ethyl acetate 0.32
    n-propanol 3.05
    acetone 1.05
    n-butanol 1.04
    acetonitrile 0.4
    DMF 38.81
    toluene 0.14
    isobutanol 0.63
    1,4-dioxane 2.37
    methyl acetate 0.53
    THF 3.52
    2-butanone 0.88
    n-pentanol 0.57
    sec-butanol 0.74
    n-hexane 0.02
    ethylene glycol 28.79
    NMP 30.3
    cyclohexane 0.04
    DMSO 45.07
    n-butyl acetate 0.3
    n-octanol 0.58
    chloroform 0.05
    n-propyl acetate 0.23
    acetic acid 17.45
    dichloromethane 0.05
    cyclohexanone 1.58
    propylene glycol 19.44
    isopropyl acetate 0.22
    DMAc 30.84
    2-ethoxyethanol 11.12
    isopentanol 0.41
    n-heptane 0.05
    ethyl formate 0.76
    1,2-dichloroethane 0.1
    n-hexanol 0.62
    2-methoxyethanol 41.98
    isobutyl acetate 0.09
    tetrachloromethane 0.03
    n-pentyl acetate 0.5
    transcutol 14.44
    n-heptanol 0.98
    ethylbenzene 0.08
    MIBK 0.29
    2-propoxyethanol 9.42
    tert-butanol 0.64
    MTBE 0.14
    2-butoxyethanol 6.2
    propionic acid 3.26
    o-xylene 0.14
    formic acid 73.72
    diethyl ether 0.35
    m-xylene 0.11
    p-xylene 0.06
    chlorobenzene 0.04
    dimethyl carbonate 2.13
    n-octane 0.03
    formamide 63.01
    cyclopentanone 2.84
    2-pentanone 0.52
    anisole 0.25
    cyclopentyl methyl ether 0.74
    gamma-butyrolactone 4.56
    1-methoxy-2-propanol 18.39
    pyridine 1.56
    3-pentanone 0.47
    furfural 4.8
    n-dodecane 0.02
    diethylene glycol 24.3
    diisopropyl ether 0.07
    tert-amyl alcohol 0.47
    acetylacetone 1.11
    n-hexadecane 0.02
    acetophenone 0.53
    methyl propionate 1.1
    isopentyl acetate 0.25
    trichloroethylene 0.18
    n-nonanol 0.64
    cyclohexanol 0.65
    benzyl alcohol 0.83
    2-ethylhexanol 0.26
    isooctanol 0.51
    dipropyl ether 0.47
    1,2-dichlorobenzene 0.05
    ethyl lactate 1.79
    propylene carbonate 1.23
    n-methylformamide 21.26
    2-pentanol 0.35
    n-pentane 0.02
    1-propoxy-2-propanol 4.44
    1-methoxy-2-propyl acetate 1.84
    2-(2-methoxypropoxy) propanol 4.69
    mesitylene 0.07
    ε-caprolactone 1.81
    p-cymene 0.1
    epichlorohydrin 1.79
    1,1,1-trichloroethane 0.02
    2-aminoethanol 26.56
    morpholine-4-carbaldehyde 26.21
    sulfolane 14.5
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.75
    n-hexyl acetate 0.54
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 7.08
    sec-butyl acetate 0.12
    tert-butyl acetate 0.31
    decalin 0.01
    glycerin 61.21
    diglyme 10.05
    acrylic acid 6.29
    isopropyl myristate 0.21
    n-butyric acid 1.68
    acetyl acetate 0.28
    di(2-ethylhexyl) phthalate 0.56
    ethyl propionate 0.28
    nitromethane 11.22
    1,2-diethoxyethane 0.99
    benzonitrile 0.26
    trioctyl phosphate 0.49
    1-bromopropane 0.05
    gamma-valerolactone 11.68
    n-decanol 0.44
    triethyl phosphate 0.42
    4-methyl-2-pentanol 0.2
    propionitrile 0.39
    vinylene carbonate 1.37
    1,1,2-trichlorotrifluoroethane 11.0
    DMS 0.89
    cumene 0.05
    2-octanol 0.38
    2-hexanone 0.29
    octyl acetate 0.41
    limonene 0.16
    1,2-dimethoxyethane 5.16
    ethyl orthosilicate 0.37
    tributyl phosphate 0.36
    diacetone alcohol 2.45
    N,N-dimethylaniline 0.35
    acrylonitrile 1.04
    aniline 0.53
    1,3-propanediol 15.8
    bromobenzene 0.02
    dibromomethane 0.03
    1,1,2,2-tetrachloroethane 0.21
    2-methyl-cyclohexyl acetate 0.37
    tetrabutyl urea 0.91
    diisobutyl methanol 0.18
    2-phenylethanol 0.88
    styrene 0.07
    dioctyl adipate 0.52
    dimethyl sulfate 4.98
    ethyl butyrate 0.33
    methyl lactate 8.58
    butyl lactate 1.92
    diethyl carbonate 0.25
    propanediol butyl ether 7.51
    triethyl orthoformate 0.54
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 1.85
    morpholine 6.06
    tert-butylamine 0.18
    n-dodecanol 0.29
    dimethoxymethane 10.88
    ethylene carbonate 0.9
    cyrene 7.1
    2-ethoxyethyl acetate 1.33
    2-ethylhexyl acetate 0.18
    1,2,4-trichlorobenzene 0.1
    4-methylpyridine 0.54
    dibutyl ether 0.24
    2,6-dimethyl-4-heptanol 0.18
    DEF 2.45
    dimethyl isosorbide 5.8
    tetrachloroethylene 0.29
    eugenol 2.73
    triacetin 1.59
    span 80 4.44
    1,4-butanediol 4.3
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 0.29
    methyl formate 9.0
    2-methyl-1-butanol 0.46
    n-decane 0.04
    butyronitrile 0.24
    3,7-dimethyl-1-octanol 0.3
    1-chlorooctane 0.1
    1-chlorotetradecane 0.04
    n-nonane 0.04
    undecane 0.03
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 1.16
    tetrahydropyran 0.84
    tert-amyl methyl ether 0.22
    2,5,8-trioxanonane 7.58
    1-hexene 0.05
    2-isopropoxyethanol 2.82
    2,2,2-trifluoroethanol 6.01
    methyl butyrate 0.4

    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