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    Chemistry

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    Also known as: 10-undecenoic acid, Undec-10-enoic acid, 112-38-9, Undecenoic acid, 10-hendecenoic acid, Desenex
    Molecular Formula
    C11H20O2
    Molecular Weight
    184.27  g/mol
    InChI Key
    FRPZMMHWLSIFAZ-UHFFFAOYSA-N
    FDA UNII
    K3D86KJ24N
    Undecylenic Acid
    Undecylenic Acid is a natural or synthetic fungistatic fatty acid, antifungal Undecylenic Acid is used topically as a zinc salt in various creams against fungal infections, eczemas, ringworm, and other cutaneous conditions. The zinc provides an astringent action, reducing rawness and irritation.
    1 2D Structure

    Undecylenic Acid

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    undec-10-enoic acid
    2.1.2 InChI
    InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
    2.1.3 InChI Key
    FRPZMMHWLSIFAZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C=CCCCCCCCCC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    K3D86KJ24N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 10-undecenoic Acid

    2. Mycodermine

    2.3.2 Depositor-Supplied Synonyms

    1. 10-undecenoic Acid

    2. Undec-10-enoic Acid

    3. 112-38-9

    4. Undecenoic Acid

    5. 10-hendecenoic Acid

    6. Desenex

    7. Renselin

    8. Declid

    9. Sevinon

    10. 9-undecylenic Acid

    11. 10-undecylenic Acid

    12. Undecyl-10-enic Acid

    13. Undecylenate

    14. Undecen-10-acid-1

    15. Undecylenic Acids

    16. Fema No. 3247

    17. Undecylenic Acid [jan]

    18. Kyselina Undecylenova

    19. 10-henedecenoic Acid

    20. 10-hendecenoic

    21. Desenex, Solution

    22. Nsc 2013

    23. N-undecylenic Acid

    24. Omega-undecenoic Acid

    25. Cruex (tn)

    26. Omega-hendecenoic Acid

    27. Chebi:35045

    28. Nsc-2013

    29. 1333-28-4

    30. 10-undecenoic Acid, 98%

    31. Undecylenic Acid (jan/usp)

    32. K3d86kj24n

    33. 10-undecenoic Acid, Homopolymer

    34. Nsc2013

    35. Undesine

    36. C11:1n-1

    37. 96451-28-4

    38. Ncgc00159425-02

    39. Ncgc00159425-04

    40. Desenex Solution

    41. Dsstox_cid_15001

    42. Dsstox_rid_79235

    43. Dsstox_gsid_35001

    44. Caswell No. 901

    45. Undecenoicacid

    46. Undecenoic Acid, Omega-

    47. Hendecenoic Acid, Omega-

    48. Cas-112-38-9

    49. Kyselina Undecylenova [czech]

    50. Einecs 203-965-8

    51. Mfcd00004442

    52. Epa Pesticide Chemical Code 085501

    53. Brn 1762631

    54. Unii-k3d86kj24n

    55. Kyselina 9-decen-1-karboxylova [czech]

    56. Undecylenic Acid [usp:jan]

    57. Undecelinic Acid

    58. Undecylenic-acid

    59. Ai3-02065

    60. Kyselina 9-decen-1-karboxylova

    61. Undecylenenic Acid

    62. 10-undecensaeure

    63. 10-undecenic Acid

    64. Einecs 215-583-9

    65. Undecen-10-saeure

    66. N-undecylenic Acid (10-1)

    67. Zinc Undecylenate (undecylenic Acid)

    68. 10-undeceneoic Acid

    69. Acide 10-undecylique

    70. Acido 10-undecenoico

    71. Acide 10-undecanoique

    72. Undecylenic Acid, Usan

    73. Ec 203-965-8

    74. Nciopen2_002642

    75. Undecylenate [vandf]

    76. Wln: Qv9u1

    77. Schembl17827

    78. 4-02-00-01612 (beilstein Handbook Reference)

    79. Undecylenic Acid [ii]

    80. Undecylenic Acid [mi]

    81. Undecylenic Acid [inci]

    82. Chembl1276010

    83. Dtxsid8035001

    84. Undecenoic Acid [mart.]

    85. Undecylenic Acid [vandf]

    86. Fema 3247

    87. Undecylenic Acid, >=95%, Fg

    88. Undecylenic Acid, >=96%, Fg

    89. Undecylenic Acid [usp-rs]

    90. Undecylenic Acid [who-dd]

    91. Hms2093l21

    92. Pharmakon1600-01505468

    93. 10-undecenoic Acid [fhfi]

    94. Hy-b0914

    95. Zinc1577120

    96. Tox21_111657

    97. Tox21_300383

    98. Bbl027462

    99. Bdbm50248304

    100. Lmfa01030036

    101. Nsc759153

    102. S9452

    103. Stk801548

    104. Akos009031595

    105. Tox21_111657_1

    106. Ccg-213461

    107. Db11117

    108. Nsc-759153

    109. Pb48616

    110. Undecylenic Acid [ep Monograph]

    111. 10-undecenoic Acid, Analytical Standard

    112. Undecylenic Acid [usp Monograph]

    113. Ncgc00159425-03

    114. Ncgc00159425-05

    115. Ncgc00159425-09

    116. Ncgc00254296-01

    117. Undecylenic Acid, Natural, >=97%, Fg

    118. Nci60_001670

    119. Sbi-0206806.p001

    120. Sbi-0206806.p002

    121. Ft-0607203

    122. U0007

    123. 10-undecenoic Acid, Purum, >=97.0% (gc)

    124. D02159

    125. P19683

    126. Ab00630892_02

    127. Q420346

    128. Sr-05000002050

    129. 10-undecenoic Acid, Vetec(tm) Reagent Grade, 98%

    130. Sr-05000002050-1

    131. W-200840

    132. F0001-0258

    133. Undecylenic Acid, United States Pharmacopeia (usp) Reference Standard

    134. 10-undecenoic Acid, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Usp, 98-100.5%

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 184.27 g/mol
    Molecular Formula C11H20O2
    XLogP33.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count9
    Exact Mass184.146329876 g/mol
    Monoisotopic Mass184.146329876 g/mol
    Topological Polar Surface Area37.3 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity141
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations. It is effective against _Candida albicans_. It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane.

    5.2 ATC Code

    D - Dermatologicals

    D01 - Antifungals for dermatological use

    D01A - Antifungals for topical use

    D01AE - Other antifungals for topical use

    D01AE04 - Undecylenic acid

    5.3 Absorption, Distribution and Excretion

    Absorption

    Undecylenic acid may be absorbed through the skin [MSDS].

    Route of Elimination

    No information regarding route of elimination.

    Volume of Distribution

    No information regarding volume of distribution.

    Clearance

    No information regarding clearance.

    5.4 Metabolism/Metabolites

    No information regarding metabolism.

    5.5 Biological Half-Life

    No information regarding half-life.

    5.6 Mechanism of Action

    Undecylenic acid demonstrated effectiveness against _Candida albicans_, which is an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the filamentous form with elongated hyphae. Hyphae formation is associated with active infections and virulence. A study proposed that undecylenic acid inhibits biofilm formation of _Candida albicans_ with optimal concentration above 3 mM and disrupts hyphal growth, which is the morphological transition from yeast to filamentous phase, at concentration above 4 mM. Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation. Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection. Undecylenic acid may also inhibit enzyme involved in lipid metabolism and abolish germ tube formation by carrying protons across the plasma membrane, thus altering cytoplasmic pH.

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K-6\/3 & K-7 TARAPUR MIDC,, NAVAPUR RD,KALODA NAKA,","city":"BOISAR,MAHARASHTRA","supplier":"ARKEMA","supplierCountry":"FRANCE","foreign_port":"NA","customer":"U. K. AROMATICS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"3200.00","actualQuantity":"3200","unit":"KGS","unitRateFc":"10.5","totalValueFC":"33525.3","currency":"USD","unitRateINR":"798.5","date":"02-Mar-2022","totalValueINR":"2555280","totalValueInUsd":"33525.3","indian_port":"JNPT","hs_no":"29161910","bill_no":"7709105","productDescription":"API","marketType":"REGULATED MARKET","country":"FRANCE","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLT NO. K-6\/3 & K-7 TARAPUR MIDC,, NAVAPUR RD,KALODA NAKA,"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1669919400,"product":"UNDECYLENIC ACID USP","address":"ZYDUS CORPORATE PARK, SCHEME NO 63, KHORAJ (GANDHINAGAR), NR. VAISHNODE","city":"AHMEDABAD","supplier":"PENTA INTERNATIONAL CORPORATION","supplierCountry":"UNITED STATES","foreign_port":"NA","customer":"ZYDUS LIFESCIENCES LIMITED","customerCountry":"INDIA","quantity":"6.00","actualQuantity":"6","unit":"KGS","unitRateFc":"148","totalValueFC":"1909.6","currency":"USD","unitRateINR":"26226.8","date":"02-Dec-2022","totalValueINR":"157360.73","totalValueInUsd":"1909.6","indian_port":"BOMBAY AIR","hs_no":"29349990","bill_no":"3567766","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"ZYDUS CORPORATE PARK, SCHEME NO 63, KHORAJ (GANDHINAGAR), NR. VAISHNODE"}]
    03-Feb-2021
    22-Aug-2024
    KGS
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