Alpha-Amyrin

HCID 73170

Substructure search Find similar structures

Basic information

CAS: 638-95-9
Standard SMILES: C[C@H]1[C@H](C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@H]12
InChIKey: FSLPMRQHCOLESF-SFMCKYFRSA-N
Molecular formula: C30H50O
Average molar mass: 426.7 g/mol
Monoisotopic mass: 426.38616621

Overview

Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane.

Names & identifiers

Preferred name: Alpha-Amyrin
IUPAC: (3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-ol
English name: alpha-Amyrin
Molecular formula: C30H50O
Molecular weight: 426.73

Names & synonyms

alpha-Amyrin638-95-9Viminalolalpha-Amyrine5alpha-urs-12-en-3beta-ol(3beta)-urs-12-en-3-ol30ZAG40J8N(3S,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-olCHEBI:10213DTXSID701025612NSC-1147874,4,6a,6b,8a,11,12,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

Show more names

α-AmyrineUrs-12-en-3β-ol, Viminalolα-Amyrine-AmyrinAMYRIN, A-alfa-Amyrinα-Amyrin-RM

RefChem:27236DTXCID801509877211-352-1Urs-12-en-3beta-ola-amyrinCHEMBL455357.alpha.-Amyrenol(3.beta.)-Urs-12-en-3-ol

Database identifiers

CAS: 638-95-9
PubChem CID: 73170
DTXSID: DTXSID701025612
ChEMBL: CHEMBL455357
ChEBI: CHEBI:10213
UNII: 30ZAG40J8N
EC Number: 211-352-1
Nikkaji: J6.928K

Properties

Computed structural properties

XLogP: 9
Topological polar surface area: 20.2 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 31
Formal charge: 0
Complexity: 779

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]

Physicochemical properties

Melting point: 178 · 178-183°C
alpha: 17 · D17 +91.6° (c = 1.3 in benzene)
Boiling point: 0.7 · bp0.7 243°
Density: 0.96 · 0.9600 (rough estimate)
refractive index: 1.491 · 1.4910 (estimate)
solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
form: Solid
pka: 15.18 · 15.18±0.70(Predicted)
color: White to off-white
optical activity: 93.3 · +93.3 (c 5.55, C6H6)
BRN: 1916550 · 1916550
Major Application: food and beverages
Cosmetics Ingredients Functions: SKIN PROTECTINGSKIN CONDITIONING - MISCELLANEOUS
InChIKey: FSLPMRQHCOLESF-SFMCKYFRSA-N
SMILES: C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C
LogP: 10.636 · 10.636 (est)
CAS DataBase Reference: 638 · 638-95-9(CAS DataBase Reference)
FDA UNII: 30 ZAG40J8N · 30ZAG40J8N
NIST Chemistry Reference: «ALPHA»-amyrin(638-95-9)
EPA Substance Registry System: -12 · Urs-12-en-3-ol, (3.beta.)- (638-95-9)
UNSPSC Code: 85151701 · 85151701
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P501
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312-P501

Chemistry & industry

Applications

Usesa-Amyrin is a natural chemical compound of the triterpene class. It is a pentacyclic triterpenol widely distributed in nature and has been isolated from a variety of plant sources such as epicuticular wax.

Upstream & downstream products

Upstream raw materials

Lupeol psi-taraxasterol

Suppliers100 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]

济南药德生物科技有限公司17805033575; 17805033575 · [email protected]

Additional notes

DefinitionChEBI: A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.

Related reactions

0 records

New reaction record

No reaction records under the current filter.

Compound notes

Loading…