Basic information
- CAS
2922-42-1- Standard SMILES
O=C(O)C1=CC(=O)[C@@H](O)[C@H](O)C1- InChIKey
SLWWJZMPHJJOPH-PHDIDXHHSA-N- Molecular formula
- C7H8O5
- Average molar mass
- 172.13 g/mol
- Monoisotopic mass
- 172.03717335
Names & identifiers
- Preferred name
- 3-Dehydroshikimate
- IUPAC
- (4S,5R)-4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid
- English name
- (-)-3-Dehydroshikimic acid
- Molecular formula
- C7H8O5
- Molecular weight
- 172.14
Names & synonyms
3-dehydroshikimate(4S,5R)-4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid(4S,5R)-4,5-bis(oxidanyl)-3-oxidanylidene-cyclohexene-1-carboxylic acidCHEBI:16630(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylateRefChem:9365127655-56-72922-42-1(-)-3-dehydroshikimic acid(-)-3-Dehydro Shikimic Acid3-dehydroshikimic acid(4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
Show more names
DHS3-DHS4,5-dihydroxy-3-oxocyclohexene-1-carboxylic acid5-DEHYDROSHIKIMIC ACIDShikimic Acid Impurity 8(-)-3-DehydroShikimicAci4,5-DIHYDROXY-3-OXO TRANS(?)-3-Dehydro Shikimic Acid
1-Cyclohexene-1-carboxylic acid, 4,5-dihydroxy-3-oxo-, (4S,5R)-Shikimic Acid Impurity 9Shikimic acid, 3-dehydro-(-)-3-DehydroShikimicAcidSCHEMBL218786orb2942912CHEBI:30918DTXSID101370235
Database identifiers
- CAS
2922-42-1- PubChem CID
- 439774
- DTXSID
DTXSID701030506- ChEBI
CHEBI:30918- EC Number
- 634-499-7
- Nikkaji
- J412.314J
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 255
Experimental & physicochemical properties
Collision Cross Section
132 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；149.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
136.77 Ų [M-H]- [CCS Type: DT; Method: stepped-field]；132.73 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
149.2 Ų [M+Na]+；131.9 Ų [M+H]+；132.2 Ų [M-H]-
Physicochemical properties
- Melting point
- 150 · 150-152 °C
- Boiling point
- 405.1 · 405.1±45.0 °C(Predicted)
- Density
- 1.713 · 1.713±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- pka
- 3.03 · 3.03±0.60(Predicted)
- color
- Off-White to Beige
- optical activity
- -59 · [α]/D -59.0±3.0°, c = 1 in ethanol
Safety & regulation
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 36
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
UsesA metabolite of Shikimic Acid
Uses3-Dehydroshikimic acid is a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid. 3-Dehydroshikimic acid has been used in a study to describe the synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester. 3-Dehydroshikimic acid has also been used in studies to evaluate the shikimate biosynthetic pathway, in order to develop nontoxic antimicrobial agents, herbicides, and antiparasite drugs.
Upstream & downstream products
Downstream products
Suppliers55 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587
云南西力生物技术股份有限公司0871-65217109 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Related reactions
3 records
Compound notes
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