[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-

Modify Date: 2024-02-19 09:17:03

[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)- Structure
[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)- structure
Common Name [7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-
CAS Number 35287-69-5 Molecular Weight 638.57200
Density 1.67g/cm3 Boiling Point 846ºC at 760 mmHg
Molecular Formula C32H30O14 Melting Point N/A
MSDS N/A Flash Point 273.7ºC

 Use of [7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)-


Secalonic acid D is a toxic compound against tumor cells. Secalonic acid D can be isolated from the metabolites of Aspergillus aculeatus. Secalonic acid D activates GSK3-β, and degrades β-catenin. Thus, Secalonic acid D down-regulates c-Myc expression, arrests cell cycle at G1 phase, induces cell apoptosis[1][2].

 Names

Name (7,7'-Bi-4aH-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3S-[3.α.,4.β.,4a.β.,7(3'r*,4's*,4'as*)]]
Synonym More Synonyms

  Biological Activity

Description Secalonic acid D is a toxic compound against tumor cells. Secalonic acid D can be isolated from the metabolites of Aspergillus aculeatus. Secalonic acid D activates GSK3-β, and degrades β-catenin. Thus, Secalonic acid D down-regulates c-Myc expression, arrests cell cycle at G1 phase, induces cell apoptosis[1][2].
Related Catalog
In Vitro Secalonic acid D (0.1-1 μM; 72 h) 在 HL60 和 K562 中以浓度依赖性方式抑制细胞增殖,IC50 分别为 0.38 μM 和 0.43 μM[1]。 Secalonic acid D (0.3 μM; 12 h, 24 h) 导致细胞周期停滞在 G1 期,(1.2 μM; 0-72 h) 并诱导 HL60 和 K562 细胞凋亡[1]。 Apoptosis Analysis[1] Cell Line: HL60 and K562 cells Concentration: 1.2 μM Incubation Time: 0, 24, 48 and 72 h Result: Induced cell apoptosis via arresting cell cycle at G1 phase. As well as, down-regulated the expression level of c-Myc. Western Blot Analysis[1] Cell Line: HL60 and K562 cells Concentration: 1.2 μM Incubation Time: 0, 24, 48 and 72 h Result: Dose-dependently decreases the level of Caspase-1.
References

[1]. Andersen R, et al. Secalonic acids D and F are toxic metabolites of Aspergillus aculeatus. J Org Chem. 1977 Jan 21;42(2):352-3.  

[2]. Zhang JY, et al. Secalonic acid D induced leukemia cell apoptosis and cell cycle arrest of G(1) with involvement of GSK-3beta/beta-catenin/c-Myc pathway. Cell Cycle. 2009 Aug;8(15):2444-50.  

 Chemical & Physical Properties

Density 1.67g/cm3
Boiling Point 846ºC at 760 mmHg
Molecular Formula C32H30O14
Molecular Weight 638.57200
Flash Point 273.7ºC
Exact Mass 638.16400
PSA 226.58000
LogP 2.16420
Index of Refraction 1.725

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EC2460000
CHEMICAL NAME :
(7,7'-Bi-4aH-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8, 8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, (3S-(3-alpha,4-beta,4a-beta, 7(3'R,4'S,4'aS)))
CAS REGISTRY NUMBER :
35287-69-5
LAST UPDATED :
199609
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C32-H30-O14
MOLECULAR WEIGHT :
638.62

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
26500 ug/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - changes in pulmonary vascular resistance Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Skin and Appendages - hair
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg/5D-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - chronic pulmonary edema Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - respiratory system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
15 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
15 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
25 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - delayed effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
lactating female 10 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
45 mg/kg
SEX/DURATION :
female 7-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
30 mg/kg
REFERENCE :
JEPTDQ Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 4(5-6),31,1980

 Safety Information

Hazard Codes T+
Risk Phrases 28
RIDADR UN 2811 6.1/PG 2

 Synonyms

SECALONIC ACID D FROM PENICILLIUM*OXALICUM
ergochrome EE
secalonicacidd
secalonic acid D1
sad
Secalonsaeure D