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123-99-9 molecular structure
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nonanedioic acid

ChemBase ID: 430
Molecular Formular: C9H16O4
Molecular Mass: 188.22094
Monoisotopic Mass: 188.10485899
SMILES and InChIs

SMILES:
OC(=O)CCCCCCCC(=O)O
Canonical SMILES:
OC(=O)CCCCCCCC(=O)O
InChI:
InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChIKey:
BDJRBEYXGGNYIS-UHFFFAOYSA-N

Cite this record

CBID:430 http://www.chembase.cn/molecule-430.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
nonanedioic acid
IUPAC Traditional name
azelaic acid
Brand Name
Azelex
Emerox 1110
Emerox 1144
Emery's L-110
Finacea
Finevin
Skinoren
Synonyms
n-Nonanedioic acid
Nonanedioic acid
Lepargylic acid
Heptanedicarboxylic acid
Azalaic Acid
Anchoic acid
Azelainic acid
Azelaic Acid
Nonanedionic acid
1,7-Heptanedicarboxylic acid
Azelaic acid
杜鹃花酸
壬二酸
CAS Number
123-99-9
EC Number
204-669-1
MDL Number
MFCD00004432
Beilstein Number
1101094
Merck Index
14905
PubChem SID
46506284
24891477
24278221
160963893
PubChem CID
2266
CHEBI ID
48131
ATC CODE
D10AX03
CHEMBL
1238
Chemspider ID
2179
DrugBank ID
DB00548
KEGG ID
D03034
Unique Ingredient Identifier
F2VW3D43YT
Wikipedia Title
Azelaic_acid

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.1478105  H Acceptors
H Donor LogD (pH = 5.5) -0.1637566 
LogD (pH = 7.4) -3.6534874  Log P 1.8243604 
Molar Refractivity 46.542 cm3 Polarizability 18.41525 Å3
Polar Surface Area 74.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.37  LOG S -1.92 
Solubility (Water) 2.28e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2.14 g/L in water expand Show data source
2400 mg/L (20 oC) expand Show data source
Apperance
Crystalline expand Show data source
Melting Point
109-111 °C expand Show data source
109-111 °C(lit.) expand Show data source
109-111°C expand Show data source
ca 102°C expand Show data source
Boiling Point
286 °C at 100 mmHg expand Show data source
286 °C/100 mmHg(lit.) expand Show data source
286.5°C expand Show data source
286.5°C @ 100 mm expand Show data source
286°C/100mm expand Show data source
287°C expand Show data source
Flash Point
210 °C expand Show data source
215°C(419°F) expand Show data source
410 °F expand Show data source
Density
1.029 g/ml expand Show data source
1.225 expand Show data source
Vapor Pressure
<1 mmHg ( 20 °C) expand Show data source
Vapor Density
6.5 (vs air) expand Show data source
Hydrophobicity(logP)
1.7 expand Show data source
pKa
4.550, 5.498 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
CM1980000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
1 expand Show data source
Risk Statements
R:36/37/38 expand Show data source
Safety Statements
S:20-25-26-37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Topical expand Show data source
Bioavailability
Very low expand Show data source
Half Life
12 hours expand Show data source
Legal Status
Rx-only (US) expand Show data source
Purity
~85% (GC) expand Show data source
~90% expand Show data source
>97% expand Show data source
≥99.0% (GC) expand Show data source
80% expand Show data source
95% expand Show data source
96% expand Show data source
98% expand Show data source
tech. 80% expand Show data source
Grade
PRACTICAL expand Show data source
puriss. expand Show data source
technical expand Show data source
technical grade expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
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Linear Formula
HO2C(CH2)7CO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05225943 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02100855 external link
Crystalline
Purity: >97%
MP Biomedicals - 02150408 external link
Practical Grade
Purity: ~90%
Crystalline
MP Biomedicals - 05215098 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00548 external link
Item Information
Drug Groups approved
Description Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
Indication For the topical treatment of mild-to-moderate inflammatory acne vulgaris.
Pharmacology Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
Toxicity Oral LD50 in rat: >5 g/kg
Affected Organisms
Various aerobic and anaerobic microorganisms
Biotransformation Mainly excreted unchanged in the urine but undergoes some b-oxidation to shorter chain dicarboxylic acids.
Absorption Approximately 4% of the topically applied azelaic acid is systemically absorbed.
Half Life The observed half-lives in healthy subjects are approximately 45 minutes after oral dosing and 12 hours after topical dosing, indicating percutaneous absorption rate-limited kinetics.
Elimination Azelaic acid is mainly excreted unchanged in the urine, but undergoes some ?-oxidation to shorter chain dicarboxylic acids.
External Links
RxList
PDRhealth
Drugs.com
Sigma Aldrich - 246379 external link
Packaging
25, 100 g in poly bottle
Sigma Aldrich - A96150 external link
Packaging
2 kg in poly bottle

REFERENCES

REFERENCES

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PATENTS

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