alpha-santonin
eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-
Identification
| Name | alpha-santonin |
| IUPAC | (3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione |
| CAS Number | 481-06-1 |
| EINECS | 207-560-7 |
| FDA UNII | 1VL8J38ERO |
| Molecular Formula | C15 H18 O3 |
| Molecular Weight | 246.30606000 |
| MDL Number | MFCD00135865 |
| Beilstein | 0089489 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 175.00 °C. @ 760.00 mm Hg |
| Boiling Point | 423.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 373.00 °F. TCC ( 189.70 °C. ) (est) |
| logP (o/w) | 1.600 (est) |
| Soluble in | water, 753.1 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | unreported-man LDLo 15 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02213']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for alpha-santonin usage levels up to | not for fragrance use. |
| Recommendation for alpha-santonin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-
11-epiiso
eusantona-1,4-dienic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone
naphtho(1,2-b)puran-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-
(3S)-2,3,3a,4,5,5a,8,9bbeta-
octahydro-3,5abeta,9-trimethylnaphtho(1,2-b)furan-2,8-dion
santonin
santoninum
semenen
(3aS,5aS,9bS)-3,5a,9-
trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
PubMed:
Synthesis and structure-activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages.
PubMed:
[Sesquiterpenoids from Solanum lyratum].
PubMed:
New eudesmane-type sesquiterpenoid from Solanum lyratum with cytotoxic activity.
PubMed:
Induction of Gâ/M arrest, caspase activation and apoptosis by α-santonin derivatives in HL-60 cells.
PubMed:
Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin.
PubMed:
Total syntheses of ainsliadimer B and gochnatiolides a and B.
PubMed:
Diminutive effect on T and B-cell proliferation of non-cytotoxic α-santonin derived 1,2,3-triazoles: a report.
PubMed:
8-[(2-Hy-droxy-phen-yl)imino]-3,5a,9-trimethyl-3a,4,5,5a,8,9b-hexa-hydro-naphtho-[1,2-b]furan-2(3H)-one.
PubMed:
3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one.
PubMed:
Theoretical studies on the photoinduced rearrangement mechanism of α-santonin.
PubMed:
In vitro antitrypanosomal activity of plant terpenes against Trypanosoma brucei.
PubMed:
Synthesis of novel α-santonin derivatives as potential cytotoxic agents.
PubMed:
A biomimetic total synthesis of (+)-ainsliadimer A.
PubMed:
Synthesis and cytotoxic activity of alpha-santonin derivatives.
PubMed:
Biotransformation of tetrahydro-alpha-santonins by Absidia coerulea.
PubMed:
Periplasmically located α-santonin binding factor in Sphingomonas paucimobilis strain S ATCC 43388.
PubMed:
Natural products in parallel chemistry--novel 5-lipoxygenase inhibitors from BIOS-based libraries starting from alpha-santonin.
PubMed:
The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed.
PubMed:
Seven-membered cyclic sulfite eudesmane derivatives: partial synthesis, structural determination, and enzymatic resolution.
PubMed:
Biotransformation of alpha- and 6beta-santonin by fungus and plant cell cultures.
PubMed:
Biotransformation of alpha-santonin by cell suspension cultures of five plants.
PubMed:
Microbial transformations of alpha-santonin.
PubMed:
A new sensitive isotropic-anisotropic separation experiment-SPEED MAS.
PubMed:
Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides.
PubMed:
Convenient method for determining the absolute configuration of chiral alcohols with racemic 1H NMR anisotropy reagent, M(alpha)NP acid: use of HPLC-CD detector.
PubMed:
Biotransformation of two cytotoxic terpenes, alpha-santonin and sclareol by Botrytis cinerea.
PubMed:
Santonin-related compound 2 inhibits the expression of ICAM-1 in response to IL-1 stimulation by blocking the signaling pathway upstream of I kappa B degradation.
PubMed:
Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives.
PubMed:
Synthetic studies of sesquiterpenes with a cis-fused decalin system, 5. A synthetic approach to the study of structure-activity relationships of the termiticidal norsesquiterpenoids, chamaecynone and related compounds.
PubMed:
Use of high-performance liquid chromatographic peak deconvolution and peak labelling to identify antiparasitic components in plant extracts.
PubMed:
Elimination of broad-host range plasmid vectors in Escherichia coli by curing agents.
PubMed:
Studies on the synthesis of sesquiterpene lactones, 12. Synthesis of (+)-colartin, (+)-arbusculin A, and their C-4 epimers and their biological activities.
PubMed:
Growth, terpenoid production and antibacterial activity of an in vitro culture of the liverwort Fossombronia pusilla.
PubMed:
Elimination of ColE1 group (pBR322 and pBR329) plasmids in Escherichia coli by alpha-santonin.
PubMed:
Antipyretic activity of alpha- and beta-santonin.
PubMed:
Mechanism of uptake of alpha-santonin by Pseudomonas cichorii strain S.
PubMed:
alpha-Santonin 1,2-reductase and its role in the formation of dihydrosantonin and lumisantonin by Pseudomonas cichorii S.
PubMed:
Antimalarial agents. 1. alpha-Santonin-derived cyclic peroxide as potential antimalarial agent.
PubMed:
Studies on microbial transformations. XVIII. Microbiological transformation of 1-alpha-santonin.
PubMed:
[Studies on the microbiological transformation of alpha-santonin and its analogues (author's transl)].
PubMed:
Sesquiterpenoids. 3. The stereochemistry of santonin: x-ray analysis of 2-bromo-alpha-santonin.