Introduction：Basic information about CAS 6754-13-8|Helenalin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Helenalin |
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| CAS Number | 6754-13-8 | Molecular Weight | 262.30100 |
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| Density | 1.25g/cm3 | Boiling Point | 473ºC at 760 mmHg |
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| Molecular Formula | C15H18O4 | Melting Point | 167-168ºC |
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| MSDS | / | Flash Point | 179.9ºC |
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Names
| Name | helenalin |
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| Synonym | More Synonyms |
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Helenalin BiologicalActivity
| Description | Helenalin is an anti-inflammatory sesquiterpene lactone. Helenalin selectively inhibits transcription factor NF-κB by directly targeting p65. Helenalin has alkylating activity, targets the cysteine sulfhydryl groups in the p65 subunit of NF-κB, thereby inhibits its DNA binding[1][2]. |
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| Related Catalog | Research Areas >>CancerResearch Areas >>Inflammation/Immunology |
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| In Vitro | Helenalin (10 μM; 20-120 minutes) causes complete inhibition of NF-κB DNA binding after 80 minutes[1]. The anti-inflammatory, anti-carcinogenic phytochemical, Helenalin is a potent inhibitor of periodic Skp2 accumulation, an F-box protein mediating SCF E3 ligase ubiquitylation and degradation of both CKIs during S phase progression[3]. Western Blot Analysis[1] Cell Line: Jurkat T cells Concentration: 10 μM Incubation Time: 20-120 minutes Result: Caused complete inhibition of NF-κB DNA binding after 80 minutes. |
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| In Vivo | Helenalin (25 mg/kg; i.p.; 6 to 12 hours) administers to immature male ICR mice caused a rapid decrease in hepatic glutathione levels[2]. Animal Model: Immature male ICR mice[2] Dosage: 25 mg/kg Administration: i.p.; 6 to 12 hours Result: Caused a rapid decrease in hepatic glutathione levels. |
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| References | [1]. Merrill JC, et al. Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin. J Toxicol Environ Health. 1988;23(2):159-69. [2]. Lyss G, et al. The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-kappaB by directly targeting p65. J Biol Chem. 1998 Dec 11;273(50):33508-16. [3]. Fernandes KM, et al. Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyteproliferation. J Cell Biochem. 2008 Oct 15;105(3):913-21. |
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Chemical & Physical Properties
| Density | 1.25g/cm3 |
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| Boiling Point | 473ºC at 760 mmHg |
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| Melting Point | 167-168ºC |
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| Molecular Formula | C15H18O4 |
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| Molecular Weight | 262.30100 |
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| Flash Point | 179.9ºC |
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| Exact Mass | 262.12100 |
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| PSA | 63.60000 |
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| LogP | 1.24630 |
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| Index of Refraction | 1.565 |
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| InChIKey | ZVLOPMNVFLSSAA-XEPQRQSNSA-N |
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| SMILES | C=C1C(=O)OC2CC(C)C3C=CC(=O)C3(C)C(O)C12 |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- BD9630000
- CHEMICAL NAME :
- Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
- CAS REGISTRY NUMBER :
- 6754-13-8
- BEILSTEIN REFERENCE NO. :
- 0028081
- LAST UPDATED :
- 199712
- DATA ITEMS CITED :
- 12
- MOLECULAR FORMULA :
- C15-H18-O4
- MOLECULAR WEIGHT :
- 262.33
- WISWESSER LINE NOTATION :
- T C575 DYVO MV KUTJ A1 BQ DU1 I1
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 125 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 150 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 10 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Gastrointestinal - peritonitis
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 90 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - hamster
- DOSE/DURATION :
- 85 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - domestic
- DOSE/DURATION :
- 100 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 45 mg/kg/3D-I
- TOXIC EFFECTS :
- Liver - changes in liver weight Endocrine - changes in spleen weight Endocrine - changes in thymus weight
- TYPE OF TEST :
- DNA inhibition
MUTATION DATA - TYPE OF TEST :
- Cytogenetic analysis
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 780 ppb
- REFERENCE :
- BSECBU Biochemical Systematics and Ecology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.2- 1974- Volume(issue)/page/year: 13,365,1985
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Safety Information
| RIDADR | UN 2811 |
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| Packaging Group | III |
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| Hazard Class | 6.1(b) |
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Synonyms
| dl-Mexicanin I |
| Helenalin A |
| HELENALIN |
| PF 56 |
| (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione |
