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Protoanemonin

HCID 66948
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
108-28-1
Standard SMILES
C=C1C=CC(=O)O1
InChIKey
RNYZJZKPGHQTJR-UHFFFAOYSA-N
Molecular formula
C5H4O2
Average molar mass
96.08 g/mol
Monoisotopic mass
96.02112937

Overview

Protoanemonin is a butenolide.

Names & identifiers

Preferred name
Protoanemonin
IUPAC
5-methylidenefuran-2-one
English name
5-methylenefuran-2(5H)-one
Molecular formula
C5H4O2
Molecular weight
96.08406

Names & synonyms

Protoanemonin5-Methylenefuran-2(5H)-one108-28-15-methylene-2(5H)-furanone5-methylidenefuran-2-one4-Methylenebut-2-en-4-olideISOMYCINcis-4-Methylenebut-2-en-4-olide66FQZ1A5SOCHEBI:28906DTXSID101483465-methylene-2-furanone
Show more names
5-methylenefuran-2-one5-methylene-5H-furan-2-one
RefChem:176665DTXCID8070837203-567-4Protoanemonene2(5H)-Furanone, 5-methylene-UNII-66FQZ1A5SO2,4-PENTADIEN-4-OLIDEEINECS 203-567-4

Database identifiers

CAS
108-28-1
PubChem CID
66948
DTXSID
DTXSID10148346
ChEBI
CHEBI:28906
UNII
66FQZ1A5SO
EC Number
203-567-4
Nikkaji
J10.112E

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
7
Formal charge
0
Complexity
144

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
1.5 · bp1.5 45°
Density
1.14 · 1.1400
refractive index
1.4945 · 1.4945 (estimate)
LogP
-0.839 · -0.839 (est)
FDA UNII
66 FQZ1A5SO · 66FQZ1A5SO
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Skin Symptoms · 2 items

Protoanemonin is found in the fresh leaves of the plants from the Ranunculaceae family and leads to contact dermatitis. In this publication, the authors present three cases that developed phytocontact dermatitis caused by the topical use of R. arvensis as an alternative treatment method for arthralgia and palmoplantar psoriasis.

Ranunculus arvensis is used for the local treatment of joint pain, muscle pain, burns, lacerations, edema, abscess drainage, hemorrhoids, and warts among the population. The authors of this case report present three patients who developed chemical skin burns after using R. arvensis plant locally for knee pain, and noted that the skin-related toxic effects of this plant have been reported to be more in fresh plants than in dried plants. Although protoanemonin, considered as the main toxic substance, was reported to be absent in dried or boiled plants, the plant was boiled, cooled, and wrapped over the region with pain in these cases. Thus, the authors think that protoanemonin might be heat resistant.

Drug Effects during Lactation · 1 item

Anemone pulsatilla and other related species of Pulsatilla contain protoanemonin, ranunculin, and anemonin. They also contain triterpene saponins and flavonoids. The fresh plant is extremely irritating to the skin, gastrointestinal tract and mucous membranes. Allergic reactions have been reported. Homeopathic preparations of pulsatilla are reportedly used for sore nipples and mastitis, to reduce an overabundant milk supply, or to increase milk supply; however, no scientifically valid clinical trials support these uses.

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Ranunculin, a glucoside, serves as a chemotaxonomic marker in Ranunculaceae plants. When these plants are damaged, β-glucosidase triggers the conversion of ranunculin into protoanemonin through hydrolysis. Subsequently, protoanemonin undergoes cyclodimerization to form anemonin. The inherent instability of ranunculin and the rapid dimerization of protoanemonin make them unsuitable for use in biological assays. Anemonin stands out as the optimal molecule for bioassays and demonstrates diverse biological properties, including anti-inflammatory, anti-infective, and anti-oxidant effects. Anemonin's potential medical uses are enhanced by the capacity to inhibit nitric oxide synthesis and successfully counteract lipopolysaccharide-induced inflammation.

Applications

UsesProtoanemonene is a natural product[1].

Upstream & downstream products

Upstream raw materials

2(5H)-Furanone, 5-hydroxy-5-methyl-2(5H)-Furanone, 5-(hydroxymethyl)-3,4-Pentadienoic acid3,4-Pentadienoic acid, ethyl ester5-(Acetyloxy)-5-methyl-2(5H)-furanoneD-erythro-Pentonic acid, 2-deoxy-, γ-lactone, 3,5-bis(4-methylbenzoate)(S)-(-)Hydroxymethyl-3(2H)-furanone(Z)-(3)-Iodoacrylic acid3-Acetylacrylic acidalpha-Angelica lactone2-MethylfuranTrimethylsilylacetylene

Downstream products

(+/-)-1-oxaspiro[4,5]dec-7-ene

Suppliers37 total

銘瑞集團有限公司17318633522 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
欧利希(湖北)医药科技有限公司17316404525 17316404525 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]
宝鸡市辰光生物科技有限公司0917-18628616646 18628616646 · [email protected]
成都麦德生科技有限公司028-82253651 18140204969 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
广东翁江化学试剂有限公司0751-2886766 13927870850 · [email protected]
启源(广东)医药化工有限公司18026564465 · [email protected]
湖北齐飞医药化工有限公司027-59322506 18071128681 · [email protected]
BOC Sciences[email protected]
湖北扬信医药科技有限公司15374522761 · [email protected]
华阴市赛普生物科技有限公司13892502238 · [email protected]
Mensura Group Limited18780014153 · [email protected]
上海瀚香生物科技有限公司17754423994 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
成都普瑞法科技开发有限公司+86-28-82633860; +86-18080483897 · [email protected]
四川恒诚致远生物科技有限公司18113192475 18113192475 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]
Wuhan Topule Biopharmaceutical Co., Ltd+86-18327326525 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13318584237 · [email protected]
上海莫奇生物科技有限公司13341702378 · [email protected]
湖北萃园生物科技有限公司18162795156 18162795156 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
上海研纯生物医药科技有限公司4001-009266 17349750668 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
宝鸡缔都医药化工有限公司029-029-81148929 17792602132 · [email protected]
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]

Additional notes

DefinitionChEBI: Protoanemonin is a butenolide.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes