(+)-Genipin

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  • Identifiers

    CAS number
    6902-77-8

    Molecular formula
    C11H14O5

    SMILES
    COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 44.03%
    Sweet 36.45%
    Mint 25.73%
    Herbal 24.97%
    Spicy 24.22%
    Nutty 22.71%
    Green 21.5%
    Caramellic 19.99%
    Woody 19.92%
    Vanilla 17.97%

     

    Flavor
    Bitter 82.02%
    Odorless 22.58%
    Sweet-like 21.86%
    Bland 21.15%
    Very mild 20.41%
    Cedarleaf 20.24%
    Lovage 19.87%
    Seedy 19.67%
    Cotton candy 19.5%
    Parsley 19.47%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    6.44 (neutral)

    Molecular weight
    226.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    531°C

    Flash point

    • 203.56 ˚C est.

  • Synonyms

    • Genipin
    • 6902-77-8
    • (+)-Genipin
    • methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • A3V2NE52YG
    • DTXSID30894999
    • methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
    • RefChem:142877
    • DTXCID601324556
    • 636-196-5
    • 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester
    • MFCD00888600
    • ST080860
    • methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
    • CHEBI:5298
    • C09780
    • (1R,4aS,7aS)-methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
    • AC1L9CSN
    • UNII-A3V2NE52YG
    • Genipin (Standard)
    • SureCN34249
    • SCHEMBL34249
    • MLS006010198
    • CHEMBL459016
    • orb1306097
    • GLXC-06545
    • HMS3261H13
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R-(1.ALPHA.,4A.ALPHA.,7A.ALPHA.))-
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER
    • EX-A4263
    • Tox21_500516
    • BDBM50565452
    • EBC-50094
    • Genipin, >=98% (HPLC), powder
    • HY-17389R
    • s2412
    • AKOS015851487
    • AC-8847
    • CCG-221820
    • FG30976
    • LP00516
    • SDCCGSBI-0633724.P001
    • NCGC00186010-01
    • NCGC00186010-03
    • NCGC00186010-10
    • NCGC00261201-01
    • AS-18947
    • HY-17389
    • SMR001456266
    • SY015025
    • G0458
    • NS00097440
    • AB01566854_01
    • EN300-7409283
    • 902G778
    • F809725
    • Q1463401
    • BRD-K28824103-001-02-8
    • BRD-K28824103-001-04-4
    • Genipin is known as an aglycone dervied from Geniposide.
    • Z2044761865
    • (1R,4aS,7aS)-1-Hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
    • 1202641-87-9
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R,4AS,7AS)-
    • Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester
    • Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methylester, (1R,4aS,7aS)-
    • methyl (4aS,7aS,1R)-1-hydroxy-7-(hydroxymethyl)-1,5,4a,7a-tetrahydro-4aH-cyclo penta[1,2-d]pyran-4-carboxylate
    • 6902-77-8

  • Applications

    Genipin (CAS 6902-77-8) is a natural product commonly used as a crosslinking agent for biopolymers and biomaterials such as gelatin, collagen, chitosan, and alginate to form robust hydrogels, films, and coatings for tissue engineering and controlled drug delivery. It also reacts with primary amino groups to yield a characteristic blue pigment, enabling its use as a natural colorant and potential colorimetric indicator in polymer systems. In polymer and biomaterial formulations, genipin acts as a curing/stabilizing agent that improves mechanical integrity and biological stability of biopolymer matrices and adhesive interfaces. It serves as a chemical intermediate for the synthesis of genipin derivatives intended for biomedical material applications. Additionally, genipin is often evaluated for cosmetic/personal care formulations as a natural crosslinker or functional additive, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.49
    methanol 44.34
    isopropanol 9.94
    water 2.88
    ethyl acetate 8.27
    n-propanol 10.43
    acetone 16.77
    n-butanol 9.67
    acetonitrile 12.67
    DMF 145.71
    toluene 2.51
    isobutanol 6.99
    1,4-dioxane 33.47
    methyl acetate 10.99
    THF 44.19
    2-butanone 11.81
    n-pentanol 5.97
    sec-butanol 7.31
    n-hexane 0.15
    ethylene glycol 36.09
    NMP 80.65
    cyclohexane 0.5
    DMSO 199.24
    n-butyl acetate 6.1
    n-octanol 5.68
    chloroform 11.04
    n-propyl acetate 6.17
    acetic acid 45.26
    dichloromethane 12.28
    cyclohexanone 29.04
    propylene glycol 16.54
    isopropyl acetate 5.76
    DMAc 97.16
    2-ethoxyethanol 46.62
    isopentanol 10.55
    n-heptane 0.29
    ethyl formate 12.64
    1,2-dichloroethane 11.06
    n-hexanol 8.36
    2-methoxyethanol 99.55
    isobutyl acetate 3.55
    tetrachloromethane 2.53
    n-pentyl acetate 6.16
    transcutol 67.94
    n-heptanol 7.42
    ethylbenzene 1.89
    MIBK 10.09
    2-propoxyethanol 36.94
    tert-butanol 15.53
    MTBE 2.8
    2-butoxyethanol 24.2
    propionic acid 16.82
    o-xylene 3.33
    formic acid 118.07
    diethyl ether 3.58
    m-xylene 3.19
    p-xylene 2.89
    chlorobenzene 4.57
    dimethyl carbonate 16.77
    n-octane 0.22
    formamide 158.46
    cyclopentanone 41.25
    2-pentanone 11.55
    anisole 7.42
    cyclopentyl methyl ether 10.37
    gamma-butyrolactone 49.84
    1-methoxy-2-propanol 58.45
    pyridine 21.15
    3-pentanone 8.38
    furfural 58.33
    n-dodecane 0.24
    diethylene glycol 70.9
    diisopropyl ether 1.3
    tert-amyl alcohol 9.92
    acetylacetone 20.37
    n-hexadecane 0.27
    acetophenone 13.86
    methyl propionate 13.14
    isopentyl acetate 6.73
    trichloroethylene 22.78
    n-nonanol 5.89
    cyclohexanol 11.16
    benzyl alcohol 14.74
    2-ethylhexanol 4.96
    isooctanol 6.1
    dipropyl ether 3.15
    1,2-dichlorobenzene 6.08
    ethyl lactate 15.45
    propylene carbonate 21.77
    n-methylformamide 76.43
    2-pentanol 5.25
    n-pentane 0.19
    1-propoxy-2-propanol 19.68
    1-methoxy-2-propyl acetate 14.62
    2-(2-methoxypropoxy) propanol 24.81
    mesitylene 2.28
    ε-caprolactone 26.4
    p-cymene 2.4
    epichlorohydrin 47.53
    1,1,1-trichloroethane 5.19
    2-aminoethanol 32.77
    morpholine-4-carbaldehyde 85.65
    sulfolane 82.37
    2,2,4-trimethylpentane 0.2
    2-methyltetrahydrofuran 14.04
    n-hexyl acetate 8.8
    isooctane 0.18
    2-(2-butoxyethoxy)ethanol 31.54
    sec-butyl acetate 3.85
    tert-butyl acetate 8.37
    decalin 0.35
    glycerin 67.27
    diglyme 53.34
    acrylic acid 27.13
    isopropyl myristate 3.95
    n-butyric acid 19.0
    acetyl acetate 8.69
    di(2-ethylhexyl) phthalate 8.16
    ethyl propionate 6.58
    nitromethane 81.31
    1,2-diethoxyethane 9.41
    benzonitrile 11.58
    trioctyl phosphate 6.18
    1-bromopropane 2.78
    gamma-valerolactone 70.28
    n-decanol 4.33
    triethyl phosphate 7.01
    4-methyl-2-pentanol 4.8
    propionitrile 8.93
    vinylene carbonate 23.58
    1,1,2-trichlorotrifluoroethane 63.46
    DMS 11.26
    cumene 1.79
    2-octanol 4.15
    2-hexanone 6.99
    octyl acetate 5.73
    limonene 3.17
    1,2-dimethoxyethane 47.47
    ethyl orthosilicate 5.83
    tributyl phosphate 5.92
    diacetone alcohol 25.69
    N,N-dimethylaniline 7.06
    acrylonitrile 20.04
    aniline 10.31
    1,3-propanediol 42.72
    bromobenzene 3.28
    dibromomethane 5.88
    1,1,2,2-tetrachloroethane 18.01
    2-methyl-cyclohexyl acetate 8.07
    tetrabutyl urea 9.99
    diisobutyl methanol 3.34
    2-phenylethanol 13.56
    styrene 1.97
    dioctyl adipate 7.78
    dimethyl sulfate 37.16
    ethyl butyrate 5.94
    methyl lactate 30.57
    butyl lactate 11.25
    diethyl carbonate 5.61
    propanediol butyl ether 24.43
    triethyl orthoformate 6.23
    p-tert-butyltoluene 2.25
    methyl 4-tert-butylbenzoate 16.45
    morpholine 41.2
    tert-butylamine 4.25
    n-dodecanol 3.11
    dimethoxymethane 54.05
    ethylene carbonate 18.59
    cyrene 36.18
    2-ethoxyethyl acetate 12.07
    2-ethylhexyl acetate 4.75
    1,2,4-trichlorobenzene 8.35
    4-methylpyridine 16.27
    dibutyl ether 3.11
    2,6-dimethyl-4-heptanol 3.34
    DEF 24.11
    dimethyl isosorbide 35.94
    tetrachloroethylene 15.95
    eugenol 20.74
    triacetin 13.96
    span 80 18.23
    1,4-butanediol 17.75
    1,1-dichloroethane 5.0
    2-methyl-1-pentanol 7.0
    methyl formate 53.15
    2-methyl-1-butanol 8.35
    n-decane 0.38
    butyronitrile 8.41
    3,7-dimethyl-1-octanol 5.33
    1-chlorooctane 1.84
    1-chlorotetradecane 0.83
    n-nonane 0.31
    undecane 0.29
    tert-butylcyclohexane 0.25
    cyclooctane 0.27
    cyclopentanol 14.25
    tetrahydropyran 11.0
    tert-amyl methyl ether 3.82
    2,5,8-trioxanonane 41.28
    1-hexene 0.62
    2-isopropoxyethanol 23.14
    2,2,2-trifluoroethanol 40.07
    methyl butyrate 9.59

    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