alpha-santonin

eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-

CAS: 481-06-1 C15 H18 O3 MW: 246.30606000

Identification

Namealpha-santonin
IUPAC(3aS,5aS,9bS)-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
CAS Number481-06-1
EINECS207-560-7
FDA UNII1VL8J38ERO
Molecular FormulaC15 H18 O3
Molecular Weight246.30606000
MDL NumberMFCD00135865
Beilstein0089489

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 SDSView
Oral/Parenteral Toxicityunreported-man LDLo 15 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot 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

Categorynatural substances and extractives
Recommendation for alpha-santonin usage levels up tonot for fragrance use.
Recommendation for alpha-santonin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

artemisia maritima

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 G₂/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.