A dicarboxylic acid with diverse biological activities
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Azelaic Acid

Item No. 23977

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
nonanedioic acid
CAS Number
123-99-9
Synonyms
  • FA 9:1;O2
  • NSC 19493
Molecular Formula
C9H16O4
Formula Weight
188.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
OC(CCCCCCCC(O)=O)=O
InChi Code
InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChi Key
BDJRBEYXGGNYIS-UHFFFAOYSA-N
Side Chain Carbon Sum
9:0
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $31

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    50 g

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    100 g

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    250 g

    $171

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    Cayman Chemical
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    Product Description

    Azelaic acid is a naturally occurring and saturated dicarboxylic acid with diverse biological activities.1,2,3,4,5 It is a competitive inhibitor of tyrosinase, NADH dehydrogenase, succinic dehydrogenase, and reduced ubiquitinone:cytochrome C oxidoreductase in vitro.1,2 Azelaic acid inhibits the growth and colony formation of B16 murine as well as HMB2 and SK32 human melanoma cells in a concentration-dependent manner but has no effect on CHO cells.3 It decreases DNA synthesis, induces mitochondrial damage and dilation of the rough endoplasmic reticulum (RER), and reduces growth of mouse keratinocytes in a dose- and time-dependent manner.4 Azelaic acid is bacteriostatic against S. epidermidis, S. aureus, S. capitis, P. acnes, P. avidum, P. mirabilis, and C. albicans in vitro (MICs = 0.03-0.25 M).5 Formulations containing azelaic acid have been used in the treatment of acne and hyperpigmentation disorders.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nazzaro-Porro, M., and Passi, S. Identification of tyrosinase inhibitors in cultures of Pityrosporum. J. Invest. Dermatol. 71(3), 205-208 (1978).

    2. Passi, S., Picardo, M., Nazzaro-Porro, M., et al. Antimitochondrial effect of saturated medium chain length (C8-C13) dicarboxylic acids. Biochem. Pharmacol. 33(1), 103-108 (1984).

    3. Lemic-Stojcevic, L., Nias, A.H., and Breathnach, A.S. Effect of azelaic acid on melanoma cells in culture. Exp. Dermatol. 4(2), 79-81 (1995).

    4. Detmar, M., Mayer-da-Silva, A., Stadler, R., et al. Effects of azelaic acid on proliferation and ultrastructure of mouse keratinocytes in vitro. J. Invest. Dermatol. 93(1), 70-74 (1989).

    5. Nguyen, Q.H., and Bui, T.P. Azelaic acid: Pharmacokinetic and pharmacodynamic properties and its therapeutic role in hyperpigmentary disorders and acne. Int. J. Dermatol. 34(2), 75-84 (1995).