3',5'-Dimethoxy-4'-hydroxyacetophenone

Names

[ Name ]:
3',5'-Dimethoxy-4'-hydroxyacetophenone

[Synonym ]:
Ethanone,1-(4-hydroxy-3,5-dimethoxyphenyl)
3',5'-Dimethoxy-4'-Hydroxyacetophenone
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone
Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-
Acetosyringenin
3,5-Dimethoxy-4-hydroxyacetophenone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
3‘,5‘-Dimethoxy-4‘-hydroxyacetophenone
Syringylethanone
MFCD00008748
4'-Hydroxy-3',5'-dimethoxyacetophenone
EINECS 219-610-5
Acetosyringone
Acetophenone,4'-hydroxy-3',5'-dimethoxy

Biological Activity

[Description]:

Acetosyringone is a phenolic compound from wounded plant cells, enables virA gene which encodes a membrane-bound kinase to phosphorylate itself and activate the virG gene product, which stimulates the transcription of other vir genes and itself[1]. Acetosyringone enhances efficient Dunaliella transformation of Agrobacterium strains[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

Natural Products >> Phenols

[In Vitro]

[References]

[1]. Xi J, et al. Acetosyringone treatment duration affects large T-DNA molecule transfer to rice callus. BMC Biotechnol. 2018 Aug 9;18(1):48.

[2]. Srinivasan R, et al. Synergistic Action of D-Glucose and Acetosyringone on Agrobacterium Strains for Efficient Dunaliella Transformation. PLoS One. 2016 Jun 28;11(6):e0158322.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
334.7±37.0 °C at 760 mmHg

[ Melting Point ]:
124-127 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₄

[ Molecular Weight ]:
196.200

[ Flash Point ]:
131.7±20.0 °C

[ Exact Mass ]:
196.073563

[ PSA ]:
55.76000

[ LogP ]:
1.23

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.528

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AM8440000

CHEMICAL NAME :: Acetophenone, 3,5-dimethoxy-4-hydroxy-

CAS REGISTRY NUMBER :: 2478-38-8

BEILSTEIN REFERENCE NO. :: 1966119

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H12-O4

MOLECULAR WEIGHT :: 196.22

WISWESSER LINE NOTATION :: 1VR DQ CO1 EO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCTKAG Bromatologia i Chemia Toksykologiczna. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.4- 1971- Volume(issue)/page/year: 14,301,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 650 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 7,178,1964

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
AM8440000

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

The RING E3 Ligase KEEP ON GOING Modulates JASMONATE ZIM-DOMAIN12 Stability.

Plant Physiol. 169 , 1405-17, (2015)

Jasmonate (JA) signaling in plants is mediated by the JASMONATE ZIM-DOMAIN (JAZ) proteins that repress the activity of several transcription factors regulating JA-inducible gene expression. The hormon...

Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study.

J. Med. Chem. 48 , 7234-42, (2005)

In this comprehensive study on the caspase-mediated apoptosis-inducing effect of 51 substituted phenols in a murine leukemia cell line (L1210), we determined the concentrations needed to induce caspas...

Identification of rice cornichon as a possible cargo receptor for the Golgi-localized sodium transporter OsHKT1;3.

J. Exp. Bot. 66 , 2733-48, (2015)

Membrane proteins are synthesized and folded in the endoplasmic reticulum (ER), and continue their path to their site of residence along the secretory pathway. The COPII system has been identified as ...