| Identification | More | [Name]
Syringic acid | [CAS]
530-57-4 | [Synonyms]
3,5-DIMETHOXY-4-HYDROXYBENZOIC ACID
4-HYDROXY-3,5-DIMETHOXYBENZOIC ACID
AKOS BBS-00004652
GALLIC ACID 3,5-DIMETHYL ETHER
LABOTEST-BB LT00454715
RARECHEM AL BE 0102
SYRINGIC ACID
4-hydroxy-3,5-dimethoxy-benzoicaci
Benzoic acid, 4-hydroxy-3,5-dimethoxy-
Cedar acid
cedaracid
Suringic acid
Syringic acid(4-Hydroxy 3,5-dimethoxybenzoic acid)
Syringle acid
3,5-Dimethoxy-4-Hydroxybenzoic Acid 4-Hydroxy-3,5-Dimethoxybenzoic Acid
Syringic acid, 98+%
3,5-dimethyoxy-4-hydroxybenzoic acid
3,5-Dimethoxy-4-Hydroxy benzoic acid (Syringic Acid)
3,5-Dimethoxy-4-hydroxybenzoic acid 97%
SYRINGIC ACID(RG) | [EINECS(EC#)]
208-486-8 | [Molecular Formula]
C9H10O5 | [MDL Number]
MFCD00002552 | [Molecular Weight]
198.17 | [MOL File]
530-57-4.mol |
| Chemical Properties | Back Directory | [Appearance]
light brown powder | [Melting point ]
205-209 °C (lit.) | [Boiling point ]
192-193°C 14mm | [density ]
1.2539 (rough estimate) | [refractive index ]
1.4570 (estimate) | [Fp ]
192-193°C/14mm | [storage temp. ]
Store below +30°C. | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
4.33±0.10(Predicted) | [color ]
Grayish-beige to light brown | [Stability:]
Stable. Incompatible with strong bases, strong oxidizing agents. | [Water Solubility ]
5780 mg/L (25 ºC) | [BRN ]
2115262 | [Major Application]
cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care | [Cosmetics Ingredients Functions]
ANTIOXIDANT | [InChI]
1S/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12) | [InChIKey]
JMSVCTWVEWCHDZ-UHFFFAOYSA-N | [SMILES]
COc1cc(cc(OC)c1O)C(O)=O | [LogP]
1.040 | [CAS DataBase Reference]
530-57-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzoic acid, 4-hydroxy-3,5-dimethoxy-(530-57-4) | [EPA Substance Registry System]
530-57-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
DH2090000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29189090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
Syringic acid is a naturally occurring O-methylated phenolic acid that can be enzymatically degraded by some bacteria as a source of methane or methanol.1 It is also a component of phenolic extracts from various plants that have antioxidant and prooxidant activities.2 Syringic acid has been shown to inhibit aldose reductase (IC50 = 213 μg/ml), proteasome activity, and cancer cell proliferation.3,4 Phenolic extracts containing syringic acid have been shown to inhibit α-amylase and α-glucosidase activities and reduce lipid peroxidation in vitro.5 | [Chemical Properties]
light brown powder | [Uses]
antiproliferative; antifungal | [Definition]
ChEBI: A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. | [storage]
Store at -20°C | [Purification Methods]
Recrystallise syringic acid from H2O using charcoal [Bogert & Coyne J Am Chem Soc 51 571 1929, Anderson & Nabenhauer J Am Chem Soc 48 3001 1926.] The methyl ester has m 107o (from MeOH), the 4-acetyl derivative has m 190o and the 4-benzoyl derivative has m 229-232o. [Hahn & Wassmuth Chem Ber 67 2050 1934, UV: Lemon J Am Chem Soc 69 2998 1947 and Pearl & Beyer J Am Chem Soc 72 1743 1950, Beilstein 10 IV 1995.] | [References]
[1] H HARA. The 4-oxalomesaconate hydratase gene, involved in the protocatechuate 4,5-cleavage pathway, is essential to vanillate and syringate degradation in Sphingomonas paucimobilis SYK-6.[J]. Journal of Bacteriology, 2000, 182 24: 6950-6957. DOI: 10.1128/jb.182.24.6950-6957.2000
[2] MILENA COTORAS. In vitro and in vivo evaluation of the antioxidant and prooxidant activity of phenolic compounds obtained from grape (Vitis vinifera) pomace.[J]. Molecules, 2014, 19 12: 21154-21167. DOI: 10.3390/molecules191221154
[3] XIAOYONG WEI. Syringic Acid Extracted from Herba dendrobii Prevents Diabetic Cataract Pathogenesis by Inhibiting Aldose Reductase Activity.[J]. Evidence-based Complementary and Alternative Medicine, 2012, 2012: 426537. DOI: 10.1155/2012/426537
[4] KHALED Y ORABI. Selective growth inhibition of human malignant melanoma cells by syringic acid-derived proteasome inhibitors.[J]. Cancer Cell International, 2013, 13 1: 82. DOI: 10.1186/1475-2867-13-82
[5] GANIYU OBOH. Inhibition of key enzymes linked to type 2 diabetes and sodium nitroprusside induced lipid peroxidation in rats’ pancreas by phenolic extracts of avocado pear leaves and fruit.[J]. International Journal of Biomedical Science?: IJBS, 2014, 10 3: 208-216.
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