(-)-Valerenic acid

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  • Identifiers

    CAS number
    3569-10-6

    Molecular formula
    C15H22O2

    SMILES
    C[C@@H]1CC[C@H](C2=C(CC[C@H]12)C)/C=C(\C)/C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Woody 62.6%
    Dry 36.73%
    Amber 34.77%
    Powdery 32.3%
    Balsamic 31.95%
    Sandalwood 30.01%
    Sweet 29.89%
    Floral 26.88%
    Animal 26.66%
    Cedar 26.42%

     

    Flavor
    Woody 31.8%
    Sweet 26.66%
    Spicy 26.3%
    Herbal 25.42%
    Balsam 24.39%
    Odorless 22.17%
    Balsamic 21.88%
    Spice 20.61%
    Basil 20.4%
    Sandalwood 20.27%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    8.91 (weak base)

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    360°C

    Flash point

    • 168.02 ˚C est.

  • Synonyms

    • Valerenic acid
    • 3569-10-6
    • (-)-valerenic acid
    • 34NDB285PM
    • CHEBI:9921
    • DTXSID8034089
    • (2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
    • DTXCID6014089
    • (2E)-3-((4S,7R,7AR)-3,7-DIMETHYL-2,4,5,6,7,7A-HEXAHYDRO-1H-INDEN-4-YL)-2-METHYLACRYLIC ACID
    • (2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid
    • (E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
    • (2E)-3-((4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
    • (E)-3-((4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
    • RefChem:50926
    • VALERENICACID
    • MFCD00075694
    • 2-Propenoic acid,3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)-
    • C15H22O2
    • (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylic acid
    • Nardin
    • Valerenic acid (Standard)
    • UNII-34NDB285PM
    • SCHEMBL403082
    • orb1684169
    • CHEMBL1545045
    • VALERENIC ACID [USP-RS]
    • GLXC-20388
    • Valerenic acid, analytical standard
    • Tox21_200313
    • BDBM50341378
    • EX-A10774
    • AKOS024457400
    • FV71689
    • HY-103524R
    • NCGC00091912-01
    • NCGC00091912-02
    • NCGC00257867-01
    • (2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexadydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoic acid
    • 2-Propenoic acid, 3-(2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl)-2-methyl-, (4S-(4alpha(E),7beta,7aalpha))-
    • MS-23355
    • CAS-3569-10-6
    • HY-103524
    • CS-0028025
    • NS00121273
    • C09743
    • G12200
    • 569V106
    • VALERENIC ACID (CONSTITUENT OF VALERIAN) [DSC]
    • Valerenic acid - Valeriana officinalis (common valerian)
    • Valerenic acid, primary pharmaceutical reference standard
    • Valerenic acid, United States Pharmacopeia (USP) Reference Standard
    • (2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoic acid
    • (2E)-3-[(4S\,7R\,7aR)-3\,7-dimethyl-2\,4\,5\,6\,7\,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid
    • (E)-3-[(4S,7R,7AR)-3,7-DIMETHYL-2,4,5,6,7,7A-HEXAHYDRO-1H-INDEN-4-YL]-2-METHYL-PROP-2-ENOIC ACID
    • 3569-10-6

  • Applications

    (-)-Valerenic acid (CAS 3569-10-6) occurs as a key sesquiterpenoid acid and a constituent of valerian root and valerian extracts. In industry and research, it is primarily used as a phytochemical marker and analytical reference compound for quality control and standardization of valerian preparations. It is also studied as part of herbal medicine/pharmacology research to understand the activity of valerian constituents, without asserting health claims. In synthetic chemistry, (-)-valerenic acid can serve as a versatile intermediate for the preparation of valerane-type sesquiterpenoids and related derivatives. In fragrance and cosmetic research, it has been explored as a potential odorant or scent component in fragrance formulations, subject to formulation limits and regulatory considerations. Overall, its applications are centered on research, standardization, and as a substrate in organic synthesis rather than consumer-ready product ingredients.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 854.45
    methanol 1035.29
    isopropanol 730.47
    water 0.44
    ethyl acetate 795.38
    n-propanol 944.7
    acetone 803.95
    n-butanol 663.15
    acetonitrile 393.11
    DMF 1137.98
    toluene 437.27
    isobutanol 576.55
    1,4-dioxane 1019.03
    methyl acetate 571.61
    THF 1552.55
    2-butanone 875.98
    n-pentanol 302.57
    sec-butanol 519.07
    n-hexane 19.01
    ethylene glycol 94.12
    NMP 549.63
    cyclohexane 31.64
    DMSO 644.58
    n-butyl acetate 449.69
    n-octanol 71.19
    chloroform 977.81
    n-propyl acetate 314.09
    acetic acid 225.71
    dichloromethane 802.83
    cyclohexanone 730.89
    propylene glycol 154.33
    isopropyl acetate 541.21
    DMAc 712.27
    2-ethoxyethanol 479.13
    isopentanol 571.19
    n-heptane 5.86
    ethyl formate 270.04
    1,2-dichloroethane 677.02
    n-hexanol 356.11
    2-methoxyethanol 967.29
    isobutyl acetate 225.21
    tetrachloromethane 144.66
    n-pentyl acetate 218.76
    transcutol 1953.54
    n-heptanol 126.91
    ethylbenzene 148.07
    MIBK 449.14
    2-propoxyethanol 744.43
    tert-butanol 719.58
    MTBE 983.54
    2-butoxyethanol 327.05
    propionic acid 298.45
    o-xylene 210.93
    formic acid 125.81
    diethyl ether 955.88
    m-xylene 285.41
    p-xylene 157.21
    chlorobenzene 365.06
    dimethyl carbonate 248.06
    n-octane 2.8
    formamide 287.56
    cyclopentanone 941.29
    2-pentanone 822.71
    anisole 340.46
    cyclopentyl methyl ether 711.72
    gamma-butyrolactone 826.43
    1-methoxy-2-propanol 864.95
    pyridine 714.66
    3-pentanone 529.6
    furfural 539.46
    n-dodecane 2.11
    diethylene glycol 425.34
    diisopropyl ether 206.59
    tert-amyl alcohol 502.38
    acetylacetone 559.31
    n-hexadecane 2.61
    acetophenone 251.7
    methyl propionate 669.99
    isopentyl acetate 438.86
    trichloroethylene 1113.79
    n-nonanol 67.62
    cyclohexanol 381.4
    benzyl alcohol 286.0
    2-ethylhexanol 142.84
    isooctanol 109.18
    dipropyl ether 148.66
    1,2-dichlorobenzene 289.71
    ethyl lactate 127.96
    propylene carbonate 375.8
    n-methylformamide 714.06
    2-pentanol 412.29
    n-pentane 24.9
    1-propoxy-2-propanol 436.98
    1-methoxy-2-propyl acetate 519.39
    2-(2-methoxypropoxy) propanol 254.45
    mesitylene 147.59
    ε-caprolactone 632.33
    p-cymene 69.83
    epichlorohydrin 1099.22
    1,1,1-trichloroethane 490.89
    2-aminoethanol 293.43
    morpholine-4-carbaldehyde 724.18
    sulfolane 669.01
    2,2,4-trimethylpentane 16.78
    2-methyltetrahydrofuran 1057.09
    n-hexyl acetate 242.31
    isooctane 17.69
    2-(2-butoxyethoxy)ethanol 430.31
    sec-butyl acetate 265.59
    tert-butyl acetate 541.48
    decalin 18.58
    glycerin 208.42
    diglyme 701.0
    acrylic acid 207.28
    isopropyl myristate 70.07
    n-butyric acid 509.03
    acetyl acetate 251.08
    di(2-ethylhexyl) phthalate 91.9
    ethyl propionate 277.99
    nitromethane 491.08
    1,2-diethoxyethane 535.57
    benzonitrile 291.81
    trioctyl phosphate 60.26
    1-bromopropane 363.62
    gamma-valerolactone 1114.87
    n-decanol 46.3
    triethyl phosphate 85.75
    4-methyl-2-pentanol 244.47
    propionitrile 474.28
    vinylene carbonate 324.33
    1,1,2-trichlorotrifluoroethane 507.22
    DMS 251.14
    cumene 93.73
    2-octanol 72.8
    2-hexanone 312.25
    octyl acetate 93.35
    limonene 83.04
    1,2-dimethoxyethane 645.99
    ethyl orthosilicate 90.32
    tributyl phosphate 75.86
    diacetone alcohol 511.22
    N,N-dimethylaniline 191.98
    acrylonitrile 462.95
    aniline 536.55
    1,3-propanediol 478.36
    bromobenzene 347.43
    dibromomethane 529.84
    1,1,2,2-tetrachloroethane 854.25
    2-methyl-cyclohexyl acetate 157.51
    tetrabutyl urea 85.6
    diisobutyl methanol 88.53
    2-phenylethanol 287.9
    styrene 177.78
    dioctyl adipate 103.57
    dimethyl sulfate 285.61
    ethyl butyrate 205.15
    methyl lactate 219.12
    butyl lactate 184.24
    diethyl carbonate 124.53
    propanediol butyl ether 279.48
    triethyl orthoformate 145.43
    p-tert-butyltoluene 73.19
    methyl 4-tert-butylbenzoate 196.52
    morpholine 1480.68
    tert-butylamine 393.13
    n-dodecanol 31.22
    dimethoxymethane 1001.26
    ethylene carbonate 314.26
    cyrene 216.74
    2-ethoxyethyl acetate 418.34
    2-ethylhexyl acetate 299.97
    1,2,4-trichlorobenzene 339.68
    4-methylpyridine 816.11
    dibutyl ether 97.54
    2,6-dimethyl-4-heptanol 88.53
    DEF 695.57
    dimethyl isosorbide 395.77
    tetrachloroethylene 525.4
    eugenol 209.48
    triacetin 203.4
    span 80 188.45
    1,4-butanediol 141.67
    1,1-dichloroethane 676.82
    2-methyl-1-pentanol 296.66
    methyl formate 337.39
    2-methyl-1-butanol 505.18
    n-decane 4.13
    butyronitrile 448.33
    3,7-dimethyl-1-octanol 98.16
    1-chlorooctane 37.8
    1-chlorotetradecane 10.82
    n-nonane 3.55
    undecane 2.86
    tert-butylcyclohexane 19.09
    cyclooctane 10.7
    cyclopentanol 388.82
    tetrahydropyran 1178.14
    tert-amyl methyl ether 458.86
    2,5,8-trioxanonane 386.3
    1-hexene 106.93
    2-isopropoxyethanol 343.29
    2,2,2-trifluoroethanol 111.36
    methyl butyrate 318.94

    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