Dayang Chem (Hangzhou) Co., Ltd.
China
Product 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)-
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Purity: 98.0%
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35287-69-5

35287-69-5 structure

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)
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.α.,4.β.,4a.β.,7(3'r*,4's*,4'as*)]]
CAS Number: 35287-69-5
Molecular Formula: C₃₂H₃₀O₁₄
Molecular Weight: 638.57200
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2016-10-07 17:25:23
Modify Date: 2026-07-16 22:36:53
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].

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*)]]
Synonyms	lpha,4-beta,4a-beta,7(3’r,4’s,4’as))) [7,7'-Bi-4aH-xanthene]-4a,4'a-dicboxylic acid, 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,4,4') sad SECALONIC ACID D FROM PENICILLIUM*OXALICUM secalonicacidd ergochrome EE ergochromeaa(2,2’)-5-beta,6-alpha,10-beta-5’,6’-alpha,10’-beta secalonic acid D1 7’-bi-4ah-xanthene)-4a,4’a-dicboxylicacid,2,2’,3,3’,4,4’,9,9’-octahydro-( Secalonsaeure D 1,1’,4,4’,8,8’-hexahydroxy-3,3’-dimethyl-9,9’-dioxo-,dimethylester,(3s-(3-a

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	Signaling Pathways >> Apoptosis >> Apoptosis Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Cancer Signaling Pathways >> Apoptosis >> c-Myc Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3
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.

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

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

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

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