Basic information
- Standard SMILES
COc1cc(C(C)=O)ccc1O- InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N- Molecular formula
- C9H10O3
- Average molar mass
- 166.17 g/mol
- Monoisotopic mass
- 166.06299418
Names & identifiers
- Preferred name
- Acetovanillone
- IUPAC
- 1-(4-hydroxy-3-methoxyphenyl)ethanone
- English name
- Acetovanillone
- Molecular formula
- C9H10O3
- Molecular weight
- 166.17
Names & synonyms
Acetovanilloneapocynin498-02-24'-Hydroxy-3'-methoxyacetophenone1-(4-Hydroxy-3-methoxyphenyl)ethanoneAcetoguaiaconeApocynine4-Acetyl-2-methoxyphenolAcetoguaiacon1-(4-hydroxy-3-methoxyphenyl)ethan-1-oneEthanone, 1-(4-hydroxy-3-methoxyphenyl)-4-Hydroxy-3-methoxyphenyl methyl ketone
Show more names
ACETOVANILLONAcetovaniloneApocynin (Acetovanillone)3'-METHOXY-4'-HYDROXYACETOPHENONE
B6J7B9UDTRNSC-209524DTXSID7060097CHEBI:2781RefChem:552432DTXCID1040740207-854-54-HYDROXY-3-METHOXYACETOPHENONE
Database identifiers
- CAS
498-02-2- PubChem CID
- 2214
- DTXSID
DTXSID7060097- ChEMBL
CHEMBL346919- ChEBI
CHEBI:2781- UNII
- B6J7B9UDTR
- EC Number
- 207-854-5
- Nikkaji
- J13.670K
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 167
Experimental & physicochemical properties
Kovats Retention Index
1447；1503；1461；1448.3
1496；1491；1498.7；1480；1497；1539；1485；1498；1487；1539；1490；1491；1483；1484.1；1486.5；1482；1478.6；1484；1494
2676；2667；2606；2620；2620；2667；2664；2664；2623；2664；2640；2651.5；2637；2626；2638；2640；2640；2640.1
Physicochemical properties
- Melting point
- 112 · 112-115 °C (lit.)
- Boiling point
- 263 · 263-265 °C/17 mmHg (lit.)
- Density
- 1.1708 · 1.1708 (rough estimate)
- refractive index
- 1.5101 · 1.5101 (estimate)
- FLAVIS Number
- 7.142 · 07.142 | Acetovanillone
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
- pka
- 8.18 · 8.18±0.18(Predicted)
- form
- Solid
- color
- Yellow to brown
- Odor
- 100 % · at 100.00 %. faint sweet vanillin
- Odor Type
- vanilla
- biological source
- synthetic
- Water Solubility
- soluble in hot water
- Merck
- 14 · 14,741
- BRN
- 637373 · 637373
- Henry's Law Constant
- 6.3 · 6.3×103 mol/(m3Pa) at 25℃, McFall et al. (2020)
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - MISCELLANEOUS
- InChI
- 1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
- InChIKey
- DFYRUELUNQRZTB-UHFFFAOYSA-N
- SMILES
- COc1cc(ccc1O)C(C)=O
- LogP
- 1.389 · 1.389 (est)
- CAS DataBase Reference
- 498 · 498-02-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 J7B9UDTR · B6J7B9UDTR
- NIST Chemistry Reference
- 1 · Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2)
- EPA Substance Registry System
- Acetovanillone (498-02-2)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 8800000 · AM8800000
- TSCA
- TSCA listed
- HS Code
- 29145000 · 29145000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 65.7% (94 of 143) of all reports.
Warning
H315 (34.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (34.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (33.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 143 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 94 of 143 reports by companies.；There are 7 notifications provided by 49 of 143 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (34.3%)；Eye Irrit. 2 (34.3%)；STOT SE 3 (33.6%)
Regulatory information
Regulatory Information
Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AM8800000
- hs_code
- 29145000
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Uses & manufacturing
Use ClassificationFragrance Ingredients
General Manufacturing InformationEthanone, 1-(4-hydroxy-3-methoxyphenyl)-: ACTIVE
Applications
Uses4'-Hydroxy-3'-methoxyacetophenone is used as an inhibitor of nicotinamide adenine dinucleotide phosphate (NADPH) oxidase, which is an enzyme responsible for reactive oxygen species production. It is also useful in the treatment of various inflammatory diseases and atherosclerosis. Further, it shows an anti-inflammatory activity and improves endothelial function by reducing oxidative stress. In addition to this, it is used for studying nitric oxide regulated processes in plants.
UsesAcetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
General DescriptionAcetovanillone is an aromatic plant ketone, which is a selective inhibitor of NADPH oxidase. It is mainly secreted in the urine of mammals as the corresponding glucuronide conjugate.
Preparation methods
PreparationSynthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-narcotic analgesic, a non-steroidal anti-inflammatory drug, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.
Related reactions
225 records
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